Peter J Reilly CPA, Author at Think Outside the Tax Box


Peter J Reilly CPA

In 1974 Peter J Reilly graduated from the College of the Holy Cross in Worcester Mass with a plan. After serving a year in VISTA in an ill-conceived project sponsored by the Worcester Consortium for Higher Education, he commenced graduate studies in history at the University of Chicago. That did not go well so he went with the backup plan.

Three years later with a bachelors in business administration from Clark University earned while working as a hotel night auditor and controller for a travel company, he went to work for Joseph B Cohan and Associates, a large local Worcester CPA firm founded in 1917. He became expert in whatever Herb Cohan said he was an expert in. The Tax Reform Act of 1986 was big help to him since he spent more time reading than most accountants and all of a sudden everything they knew was wrong. In 1990 he was the last person to become a partner in Joseph B Cohan and Associates.

In 1997 he became one of the founding partners in CCR LLP (he was not the R), which grew to be the largest regional firms in New England, at least by their own account. The firm was acquired by Grant Thornton in 2011 giving him a taste of national firm life as a managing director. That went slightly better than graduate school in history.

After Grant Thornton was done with them Reilly and his life partner opened a boutique practice with another couple focused on real estate tax issues with a taste of family office. They withdrew from the practice 2018 and began touring the country in an RV until interrupted by the plague. They are currently sheltering in place in their home in North Oxford MA. Reilly continues to consult mostly for other tax practitioners.

Reilly’s writing career began in 2009 with a blog, now titled Your Tax Matters Partner. He was picked up by in 2011 and continues with both. Although he covers a wide range of tax topics, part of his perspective is that of a practical large local/regional CPA who has to provide technically sound advice to clients and partners who are not that patient.


How to Qualify for More Interest Deductions You Didn’t Pay

Your Questions Answered: The Dubious Anonymity of Virtual Currency Transactions

Question: Bitcoin being treated as property by the IRS was partially related to not being “legal tender in any nation.” Does the fact that El Salvador is now using cryptocurrency have any cascading ramifications for tax/currency treatment of bitcoin in the U.S.?

Answer: The Department of Justice recently issued a news release to strike terror in the hearts of anyone attempting to execute cryptocurrency tax shenanigans. Similarly, the federal court for the Northern District of California entered an order authorizing a John Doe’s summons on Payward Venture Inc. and subsidiaries d/b/a Kraken. The IRS wants to look at the records of U.S. taxpayers who conducted at least the equivalent of $20,000 in transactions in cryptocurrency during the years 2016 to 2020.
What’s with all the sudden interest in crypto, and why are the feds looking to snoop around retroactively? If you’re curious to find out why and how to stay off its radar, keep reading.

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Why Many Tax Pros Want a Stronger IRS

Early last month Adam Markowitz faced a storm of criticism over a tweet that suggested that people upset about increased IRS funding should maybe just be compliant. It got rather ugly. #TaxTwitter came to his defense despite some of us disagreeing with details of his tweet.

All of my GOP friends who are worried about 87,000 IRS enforcement agents coming after the little guy… How about just don’t cheat on tax returns? A fully truthful and accurate tax return is bulletproof in an audit. I never understood the fear of an IRS audit. Don’t lie. Period.

For somebody whose return has more than a few moving parts there is a lot of effort in putting together information for an audit. And there will usually be some things that can be viewed differently. Further you can sometimes catch the agent from hell. AFH is sure that your client is a crook and it will be hard to convince them they should go fight crime someplace else. With all that said many tax pros would still like an IRS that audits more, although they might want them to fix some other things first.

To learn more about what is expected in the coming months, learn more here.

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Way Out of State Tax on Student Debt Forgiveness

There was some rain on the parade of celebration of the student loan debt forgiveness. The Tax Foundation, perhaps with a touch of schadenfreude, announced that the forgiveness, not federally taxable due to recent legislation, might be taxable in as many as thirteen states. They have taken a closer look and backpedaled quite a bit. It is now down to four states Minnesota, Mississippi, North Carolina and Wisconsin and those are not for sure. But, there is likely another way out for many of the recipients of this boon. Keep reading to learn more!

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Using S Corporations to Minimize FICA And Medicare Tax

When United States Tax Court Judge Paris issued the opinion in the case of Ryan Fleischer in 2016 , it caused quite a stir in the tax blogosphere. And from what I have been able to gather off the record it remains of interest. The Fleischer decision makes it very difficult, if not impossible for some financial professionals to use S corporations to mitigate self-employment tax. Rather than attack on reasonable salary, the IRS took an assignment of income approach, which succeeded throwing planners for financial professionals like Fleischer into a bit of an uproar…

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US V Harry Stonehill – America’s Jarndyce v Jarndyce

1962. It was the only year in which JFK was president for the whole entire year. World events impinged on my family. My older brother served onboard an aircraft carrier chasing Soviet submarines and when not recovering Mercury astronauts, had his four-year enlistment extended to five. Somehow the bright fourth grader that I was, I missed the story of the dramatic raid by the Philippines National Bureau of Investigation on March 3, 1962. According to reporter, Amando Doronila, who covered the raid, 200 agents seized 35 truckloads of documents from 27 offices and corporations controlled by American expatriate Harry Stonehill.

Why should we care? Believe it or not, the implications of that March 3, 1962, raid are still being litigated in the United States. Read on to learn more!

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Trump Indictment: An Accountant’s Perspective

IRC § 1031 exchanges have the ability to confer substantial financial benefits to taxpayers. Although taxpayers may use § 1031 to place themselves in a superior economic position, taxpayers may not exploit this section in an abusive manner. Taxpayers can use exchanges to give themselves different types of benefits, but one of the primary benefits is the deferral of federal income tax. When conducted correctly, 1031 exchanges are regarded as a form of legitimate tax avoidance. One of the main issues involved with these transactions is determining the boundaries between abusive tax avoidance and non-abusive tax avoidance. In the context of “related party exchanges” – i.e. those transactions which involve subsection 1031(f) – this issue shows up in a relatively complex fashion, because the related party rules are not well understood by most practitioners. Furthermore, determining abusive tax avoidance with related party exchanges is difficult because of the scarcity of case law.

Based on the case law which we have, and on the other authoritative references, we can put together a reasonable overview of the risks of related party exchanges. This overview should prove useful when providing expert counsel to taxpayers seeking to conduct this type of transaction. For direct exchanges, the 2-year ownership rule found in 1031(f)(1)(C) should be used as the dominant source of guidance. For “indirect exchanges,” taxpayers must be aware of the higher levels of risk involved, as there is a greater possibility of abusive tax avoidance.

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Trump And Clinton Returns and What Regular Folk Need to Know About Carryovers

It seems like the left and the right have entered into a competition as to which side can make the silliest tax observation. The New York Times came out strong for the left as its team of reporters was handed fragments of Trump’s 1995 tax filings. They proceeded to “explain” flow-through entities and net operating losses, fairly mundane tax concepts, as if they were tools of Satan. It did not take long for the right to strike back at least as imprudently.

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Top Crime Writer Cannot Avoid SE Tax on Book Royalties

Karin Slaughter’s novel False Witness focuses on a lawyer in a prestigious Atlanta firm gearing up for a criminal trial. Coincidentally we have this week the outcome of her own legal drama, which likely only excites the tax blogosphere. Her appeal to the Eleventh Circuit of a 2019 Tax Court decision confirming that she owed almost $190,000 in self-employment tax for 2010 and 2011 was unsuccessful.

Read on to find out what we can learn from this lesson!

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The Ultimate Year End Tip Guide and the Search for the Great Shelter

Coming up on the end of the year, year end planning is kind of a ritual for me. I take my first pass in early November and will do it again no later than December. It is pretty boring. I thought it would be worthwhile to do a survey of a variety of year end tips articles. What is going on here is something like Ahab’s hunt for the great white whale. I am looking for something to help out HENRY. HENRY stands for High Earnings Not Rich Yet. I wrote about the quest in 2019. I found nothing much for HENRY then, and this year’s batch of advice articles really does not offer much.

The articles do not all say exactly the same thing, but there is a lot of commonality. Due to the sophisticated nature of the readership of TOTTB, I will just allude to the tips, not explain them in detail, because I am going someplace else with this. There is nothing dramatic for HENRY coming from conventional advisers, which accounts for HENRY’s vulnerability to sketchy tax shelters. I will share a bit about what I have seen in that department and reflect a bit.

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The Trouble with Management Companies

Management companies exist in a variety of fields for sound reasons. Real estate owners, for example, will hire a management company to collect the rent and deal with maintenance of their properties. Professional practices may use management companies to allow non-professional owners a stake in the practice. Sometimes, though, management companies are not for a real business purpose but rather as a device to shift income. It often does not end well as we will see.

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The Final Word on Hobby Loss Developments In 2021

Pedants will argue that you shouldn’t refer to Code Section 183 – Activities not Engaged in For Profit as the “hobby loss rule”, because the word hobby appears nowhere in the statute. The pedants scored a point in 2021, but I will still be sticking with the term. It looked like a slow year for hobby loss developments, but we finished with two major cases including a big taxpayer win. Let’s take a look.

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The Dealer Vs Investor Problem for Real Estate Capital Gains

I remember trying to explain the dealer versus investor concept to a would-be real estate entrepreneur. I asked him whether he was holding the property for sale. He kind of looked at me and smiled and said “Everything is for sale. It just depends on how much.”. If there is any ambiguity it is easy to know what the answer is after the fact. If there was a big gain relative to expenses then you were an investor. If there was a loss, then you were a dealer. Unfortunately, you really are not supposed to practice that way. I am going to assume that you want investor status and that you are blessed with a gain. What can you do to make sure the IRS respects your investor status?

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The Constitution for Tax Pros

A case currently before the Supreme Court, Charles Moore, G. Moore et ux. v. United States , has the court looking at some of the fundamentals of the Constitution’s treatment of taxation. Advocates of various views are hoping for an earthshaking result. Also, many “tax protester” arguments base themselves on misreading of Supreme Court decisions from around the time of the 16th Amendment. Knowing a fuller version of what surrounds the snippets they feed you probably won’t help you bring them around if they have drunk deep of the tax protester Kool-Aid, but it will help you maintain your own sanity. Let’s start with what the Moore case is about.

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The CohnReznick Lawsuit: Compliance and Planning Around the Low-Income Housing Tax Credit

A recently filed lawsuit against CohnReznick opens a window into a niche form of tax practice – compliance and planning around the Low-Income Housing Tax Credit . The case highlights a current controversy between investors seeking returns and not-for-profits seeking to insure continued affordability and their own interests to be just a bit cynical. We get to discuss some obscure tax issues and reflect on the question of who it is that is actually your client.

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The 8082 Solution to Erroneous K-1s

If you’re thinking about extra forms that might have to go in with a 1040, Form 8082 is probably not the first thing that pops into your mind. But if what you need to do includes Form 8082 – Notice of Inconsistent Treatment or Administrative Adjustment Request, and you leave it out, there might be no way to recover.

That appears to be the result in the Second Circuit decision in Laurence Gluck’s appeal of a Tax Court decision. There is also a lesson about like-kind exchanges that may have continuing significance despite changes in the law. With a deficiency of more than $1.5 million, it seems like a pretty big deal. It turns out that Laurence Gluck is one of New York City’s largest landlords, so it may not have been that big a deal for him. On the other hand, it makes it surprising that the issue tripped him up.

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The 1099 Nightmare

My attitude toward 1099 compliance changed radically about fifteen years ago. The type of 1099 compliance I am talking about is for business to business services. If you are running a bank or a brokerage house, this will not be any help. I was a partner in a regional firm and frankly I never gave 1099 compliance much thought until I was called in to consult on an audit. Then I got this really scary wake-up call…

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Tax Court Allows Defense Contractor to Claim Afghanistan as Tax Home

The “Hey, Hey Just Don’t Pay” Tax Strategy

One of the favorite sayings of my first managing partner, the late Herb Cohan, was “I’d rather owe it to you than cheat you out of it.” To be honest, like some of the other sayings, I was never clear exactly what it meant. Nonetheless, I think it sums up pretty well a tax strategy that is becoming more viable every year. File a timely accurate return and just don’t pay. Wait 10years and celebrate when the statute of limitation on collections runs out.
Did you know that not paying can be a strategy to get out of your tax bill? It can be, depending on the qualifications and your specific circumstances. Keep reading to see how to qualify.

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Tax Disaster Relief – More Than Just Return Extensions

Evie and I withdrew from active tax practice in 2018, but she maintains a sort of family and friend’s freebie practice using Drake. I help a little. We have been struggling with difficulty getting the information for one of our “clients” as we watch the ultimate October 15 deadline creeps up on us. She is in Florida in one of the counties covered by President Biden’s disaster declaration relative to Hurricane Ian. So it was sort of a relief to find out that we have another three months to get the return done.

In this case it is not a huge benefit since interest will still clock if there turns out to be a balance due, since the payment was due on April 18. “Certain deadlines” falling on or after September 23, 2022 and before February 15, 2023 are postponed through February 15, 2023.

Read on to learn more!

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Tax Days of Our Lives: CPA Firm Contentious Breakup Ends in Tax Court Decision

I am going to nominate the Clark Raymond opinion as the best tax story of the year. At least, it is the best one for CPAs. You have to tease it out of the opinion, but there is a kind of rollicking story of troubled partner relationships. I did 40 years in large local and regional public accounting with a little bit of national icing on the cake and never encountered so much apparent dysfunction. Other commentary on the case has concluded that the lesson is about doing a good job maintaining your capital accounts, but I think the real lessons may be a little different.

It is public record, but the guys in the conflict are still practicing so out of professional courtesy I will refer to them as Tom, Dick, and Harry. There is another partner who is part of the story that I will call Jane. Also, for simplicity, I will ignore the fact that they held their partnership interests through single member entities and in Tom’s case in an entity with his wife who did administrative work. And I will refer to the entity involved as “the firm.”

The story is every accountant’s nightmare (and would make for a great tax-themed soap opera). Partners disagree. Partners walk out. Clients follow exiting partners to their new business leaving the old partner with debt.

Here is the story.

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Tax Court Allows Defense Contractor to Claim Afghanistan as Tax Home

Tax Court Allows Defense Contractor to Claim Afghanistan as Tax Home

Question: We have a client who is moving out of the country, can they qualify for the foreign earned income exclusion?

Answer: Deborah C Wood owned a house in Texas but was able to convince Judge Lauber of the United States Tax Court to rule that her true home was Kandahar Airfield in Afghanistan. This saved her most of the $95,301 in additional tax that the IRS was seeking for the years 2012-2016, not to mention penalties and interest. The narrative that allowed her to win the case is worthy of study by those who represent expatriates who may qualify for the foreign earned income exclusion. There is another lesson in the case, though and that is to seek good tax advice sooner rather than later.

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Sometimes it is Clear There are Lessons, But Not Clear What They Are

A recent opinion in the ongoing litigation in the case of Clair R. Couturier makes a really important point about the distinction between a penalty and a tax. We will get to that, but I would also like to discuss the larger story of the case as I struggle with what the lesson is. I thought this case might be a good illustration of Reilly’s Second Law of Tax Planning – Sometimes it’s better to just pay the taxes – but I’m not 100 percent sure, so I will let you be the judge.

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Some of What You Need to Know to Do 1041 Right Because Nobody Knows Everything

There was a recent IRS memo from an associate chief counsel that should be shocking but actually isn’t. Promoters have for many years been hawking a “copyrighted non-grantor irrevocable complex discretionary spendthrift trust,” which purported to avoid capital gains tax. You could learn about it on TikTok. It “worked” by citing Section 643(a)(3), which excludes capital gains allocable to corpus from distributable net income. You and I both know that DNI is not taxable income, but not everybody who learns the tax law from TikTok has caught onto that subtle point yet.

Although I have never encountered anything as egregious as the “copyrighted, etc, etc, trust” I have seen a lot of problems with trusts over the years (and partnerships and SALT – don’t get me started). Much of it has to do with working under a lot of pressure. Often, the things that are wrong end up not mattering all that much, but I get a little frightened, because maybe one of these days the IRS is going to start getting its act back together. If it does, I think things may be a little shocking to practitioners who have grown up in an environment where enforcement has been progressively gutted.

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Some Harsh Lessons on Being Late from the Tax Court

Penalties for procrastination in tax matters can be somewhat harsh. Judge Albert Lauber of the United States Tax Court gave us some lessons on the topic earlier this year.

The “strategy” of over withholding so that you can file your return whenever the spirit moves you rather than by the due date has a serious downside. The statute of limitations will not work in your favor, but it will work against you. It is a little like you are playing in a chess tournament and you and your opponent are staring at the board. Your clock is ticking and theirs is not.

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Section 1244 Still Worth Remembering

The inherent optimism of entrepreneurs makes thinking about things that mitigate the effect of failure not that unpleasant. In a career in accounting, you are likely to see many deals that don’t work out, so it’s best to remember anything that will lessen the pain. Section 1244 is such a provision. Section 1244 allows what would otherwise be a capital loss to be treated as ordinary. Its significance has been somewhat diminished, but every little bit helps.

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Salt Miner’s Run for the Roses Ends with a Big Tax Bill

Judge Mark Holmes of the United States Tax Court expressed admiration for the achievements of Joseph G. Bucci Sr. whose American Rock Salt provides the salt to keep many of the streets in the Northeast passable in the winter. You can learn a bit about that from an interview in New York by Adriane Quinlan . The positive remarks were no help in the ultimate result. Judge Holmes agreed with the IRS that Bucci’s three side hustles — a real estate enterprise, a farm, and some racing horses — were “Activities not engaged in for profit” making losses unallowable. The total tab including accuracy penalties for 2016 and 2017 was $711,980. Judge Holmes explained the result in a bench opinion, which is less formal than a memo decision. The trial began in Buffalo on June 14, 2023.

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Recent Decision on S Corp Redemption Illustrates Advantage of Cross-Purchase Over Redemption

S Corp Redemption Decision Illustrates Advantage of Cross-Purchase

There are some significant lessons in the recent decision in the case of Estate of Michael Connelly. Sorry to spoil the surprise, but what I think the big one is is that co-owners of S corporations (and other sorts of entities) should consider a cross-purchase rather than redemption when they have a buy/sell agreement. That is particularly true if life insurance funds the arrangement.

Keep reading to find out why.

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Recent Hobby Loss Developments

Section 183, which limits or entirely eliminates deductions attributable to activities not entered into for profit, may be coming in for more attention from an invigorated IRS. Section 183 is commonly referred to, not without reason, as the hobby loss rule. Based on my extensive study of the case law, I believe that practitioners widely misunderstand 183. I have noted cases where taxpayers had not gotten a heads up from their adviser. More commonly there is a misunderstanding of 183(d), a presumption in favor of taxpayers that is rarely relevant at all, but which the agency can never use against them. Most important is the failure to appreciate that it is the objective of making a profit not the expectation that is necessary. With that in mind here are the most recent developments…

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Prepare For the Day When You Don’t Have More Work Than You Know What To Do With

In the last few months, I have been getting “seems like old times” feeling as interest rates rise. They remain laughably low by the standards of my early days in the business. I can remember prime being 20%. And then there are all these issues with office rentals thanks to the aftermath of the plague.

One of the nice things about a career in accounting is that while you are affected by business cycles the need for our work is somewhat continuous. I’m thinking that now might be a good time to get ahead of the curve a little and study up on a Code Section that may be coming up a lot more – Code Section 108 – Income from discharge of indebtedness. Fortunately, a recent Tax Court opinion in the case of Michael G. and Julie A. Parker can provide us with a lesson in some of the important principles in this area.

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Poor Tax Judgement Turns Junk Call Gold into Lead

Everything becomes a tax story eventually. That is what provides me with a lot of “I was today years old” experiences as tax stories are the one thing that I follow religiously. So I first learned about the field of Telephone Consumer Protection Act (TCPA) litigation from reading the proposed findings and recommended dispositions in the case of Ruben Escano v. Innovative Financial Partners LLC and Josh Benson. Innovative Financial Partners is a subsidiary of Humana.

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Passive Activity and Self-Employment Tax In Rentals – One Of These Definitions Is Not Like The Other

Somebody I consult for threw a kind of oddball fact pattern at me. Their client, “Terry,” owns a big house with many rooms in a kind of resort type area. Terry rents the rooms out on a short-term basis averaging three or four days and provides no other services. Between this and that, Terry ends up spending about 15 hours a week.

The big concern comes from Terry buying a cost segregation study, which will mean a big loss. Can Terry use the loss in the year incurred, or will it be suspended? And is the income subject to self-employment tax in the future? I thought the answers to those questions were the same, but we learned from the Chief Counsel’s Office, one of those things is not like the other.

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Notice 2019-07 250 Hour Requirement – What It Means and How to Meet It

Question: How can my rental real estate property qualify for the 199A QBI deduction?

Answer: The age-old CPA answer of “it depends” certainly applies here. To qualify for the 20 percent deduction, your enterprise has to, as a threshold, be a trade or a business. So whether a real estate rental is a trade or a business is a thing that matters like… Can analysis be worthwhile?

Real estate management companies that want to distinguish themselves should be looking at IRS Notice 2019-07. That is the main lesson of today’s post, but it also applies to tax preparers and self-sufficient owners. There is something new to keep track of, and it is a lot easier if you do it as you go rather than after the fact.

I’ve got something here for preparers and property managers, when acting sooner rather than later will be helpful. It’s theory is it is easier to collect information actively when it is fresh, rather than a year or more later as often happens in tax work.

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Monetized Installment Sale – Risky Business

The monetized installment sale (MIS), which is more of a product than a tax concept sounds very attractive. In the right circumstances MIS promises a very long deferral of capital gains tax for a reasonable cost. But does the strategy actually work?

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Monetized Installment Sale – IRS Finally Says It Does Not Work

The promoters of Monetized Installment Sales got some bad news from the IRS earlier this month. The IRS released an analysis the Office of Chief Counsel did outlining six, count them six, ways in which the transaction does not work as the promoters claim. The release will not stop the industry in its tracks, but it will probably be a relief to practitioners who have been advising that the technique is flawed.

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Maybe That Trust Really is Defective

There are times when I really would like to know the story behind the story. And that is the case with CCA 202352018. The only good thing about not knowing the story behind the story is that I get to make one up. The CCA is about one of the funniest oxymorons in the tax field. It concerns an intentionally defective grantor trust (IDGT). That is serious competition for my favorite tax oxymoron – passive activities. Let’s start out with some background on IDGT. This piece is mainly for the income tax preparers who have to deal with the implications of this fancy planning rather than the fancy planners.

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Looking Bad for Investors in Syndicated Conservation Easements

Albert Lauber, my favorite Tax Court judge, gave us an opinion in February that paints a detailed picture of the workings of a syndicated conservation easement. In the end, he supports the findings of the Senate Joint Finance Committee that the engine of these abusive transactions is an inflated appraisal. In November, David Gustafson issued an opinion that exposed the financial engineering techniques that promoters engaged in. We’ll take a look at those, but first I would like to give you an overview, because we may need that to figure out the lessons to be learned.

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Joint Filing – An Election Not a Marital Vow

The flurry of tax provisions, meant to alleviate the economic dislocation of the Covid plague, have made many tax practitioners sensitive to the possibility of Married Filing Separately yielding a lower tax for a couple. Back in the day, it was rare enough that many felt they could safely ignore it. Lindsay Starrett of Baker Starrett in Grinnell, Iowa, gave me an example of saving taxpayers $3,500.

I am not going to try to parse the details of that or other examples. I will just refer you to Reilly’s Sixth Law of Tax Planning: Don’t do the math in your head. Have good software and code income items as taxpayer, spouse, or joint. You may need to run multiple computations moving the dependent’s around. Also be aware, the IRS may not be as cooperative as it should be in allocating estimated tax payments. One of my old friends wrote me:

“In 2020, we did MFS returns for the $10,200 unemployment exclusion and learned the IRS is unable to …”

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IRS Issues Hobby Loss Audit Technique Guide

2021 had been shaping up to be a pretty slow year in the hobby loss arena until September. Then not long after Labor Day we got a revision of the audit technique guide Activities Not Engaged in for Profit Audit Technique Guide Internal Revenue Code Section. The previous update was issued in June 2009. The two documents are nor radically different, but there are some things worth noting.

I will start off with some background on Section 183, but first I will introduce you to a likely target of the revenue agents boning up on the new guide.

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Important to Maintain Substantiation for Carryovers

If you build a mini business empire and it subsequently fails, a small consolation prize might be a net operating loss carryover that will shelter some or all of your more modest income for many years. Of course NOLs are only one among many carryovers that need tracking. In my experience the tracking often leaves much to be desired. Changes in tax preparers or even software can result in the loss of valuable carryovers. But that is not the worst of it…

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How to Avoid Losing Valuable Noncash Charitable Contributions

The rules for noncash charitable contributions defy easy summary. On the other hand, they are not rocket surgery. Moving on from the humor, if you want to sum them up in a sentence you can use Reilly’s Seventh Law of Tax Planning: Read the instructions. Specifically, you want to read the instructions to Form 8283 Noncash Charitable Contributions.

There is, of course, more to it than that, but you will find a remarkable number of disallowed deductions from not following those instructions. To be fair, sometimes there are other shenanigans going on and the instruction failures are the easiest way for the IRS to attack. Nonetheless, there is nothing to say that the IRS will not use the precedents set in those cases on your client even though they are not trying to get away with anything.

To get a simplified list of what to know and implement, continue reading.

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How Things Go Criminal

If you were to ask most taxpayers what they worry about when it comes to their tax returns, they might say an unexpectedly high tax liability or even a late penalty. Next to none will worry they are at risk for criminal prosecution. There is a sound reason for this. In the fiscal year ending September 30, 2021, taxpayers filed over 261,000,000 tax returns. During that same period, IRS Criminal Investigation (CI) initiated only 2,581 investigations—a paltry 0.00098% of all tax returns filed. While CI entanglements are not a common experience, there are still lessons to be learned from looking at how things can go awry.

So what types of scenarios have resulted in criminal investigations by the IRS, and what can this teach the everyday taxpayer? First of all, working with an expert, such as a Certified Tax Planner, will help you better understand what is permissible by the IRS and reassure you that your returns are fraud-free. For a few tips on what not to do, read the cases below and review our key takeaways for each one.

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How Should a Disregarded Single Member LLC File a W-9?

Although Form W-9 has some other purposes, a company will usually ask you to fill it out if you are a business-to-business service provider . If you don’t provide a TIN to your customer, they may have to subject you to backup withholding . If it is my company that asks you for the W-9, I am not going to do backup withholding if you don’t send me the W-9. I’m just not going to pay you until you cough it up.

I believe in learning from experience. But it is better if the experience you learn from is other people’s experience. That is why a very large percentage of my tax writing is from court opinions, most often the United States Tax Court. This piece is my own experience.

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How $15,000 in Cryptocurrency Created a Half Million Dollar Tax Bill

Tax Court Docket 26425-21 can serve as a wake-up call to your clients who have been dabbling in cryptocurrency. TaxNotes has published the petition if you want to know the name and profession of the taxpayer involved, but I am just going to call him Joe. Joe is doing pretty well in his profession. Just for the heck of it he decided to dabble in crypto. He never had more than ten to fifteen thousand dollars invested in crypto. What could possibly go wrong?

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Home Sweet Domicile – There’s More to State Residence Than a Driver’s License

Voter registration, a drivers license, and day counting are what come to mind when people think about residence for state income tax purposes. There is no question that those basics are very important and ignoring them can kill your cause. Nonetheless, many other factors can enter into a determination, including church attendance and pets. That’s because you will generally be a resident of the state in which you have your “domicile.” And domicile as a concept borders on the mystical. It is your true home, it remains your domicile until you abandon it and establish a new one.

Yet, establishing your domicile in a state with no (or low) income taxes can be lucrative. In some cases, this can represent millions of dollars all by avoiding state income tax. The natural progression of a business owner’s life can also include exiting said business at substantial profit. Your domicile at the time of the transaction can be pivotal in determining how much of that profit you’ll be left with in retirement.

To learn more about how to do this, keep reading.

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Hobby Loss Developments in 2023

The laws of tax planning that I developed over my writing career that will be expounded in the upcoming Reilly’s Laws of Tax Planning, published by Think Outside the Tax Box, lean a little on the conservative side, as tax planners use the term – conservative versus aggressive, not conservative versus liberal. This results, in large part, from their primary source being court decisions.
The 18th law stands out from the others in this regard. “Honest objective trumps realistic expectation” encourages practitioners to be somewhat more aggressive in claiming losses from activities that seem a little dubious . I still hold that view, even though there have been no encouraging developments in 2023. Here is a roundup on the action last year through December 2, 2023.

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Filing Separate Returns To Maximize Credits

I have always thought of separate filing as something that filers should seriously consider for the final year of marriage or in circumstances where you think your spouse has significant audit exposure that you don’t want to share. The circumstances in which two married filing separate returns would yield a lower aggregate tax than a joint return were so rare that everyone I knew entirely discounted it. Things are different in 2021 (Also in 2020, but that is water under the bridge). What is driving the phenomenon are recovery rebate credits (which many received as economic income payments) and child tax credits.

Be sure and read this before sending those electronic returns before the 18th. You may just have some savings there. Click here to keep reading.

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Everything You Need to Know About the Fair Tax and More

As you are in the heat of another tax season, probably without enough help, you don’t have time to study legislation especially proposed legislation prospectively effective in 2025 that is extremely unlikely to pass. But you may have clients or friends or relatives who expect you to know about this sort of thing. Fortunately, you have me who retired from active practice right at the end of 2018 and has time for this sort of nonsense. So here is more than you need to know about the proposed Fair Tax Act of 2023.

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Enjoy Decades of Tax-Free Growth With a 529A

If you’re disabled or support someone who is, a 529A plan can be a powerful way to save for the future. Potential earnings grow tax-free, and you won’t have to pay taxes when you withdraw, as long as the withdrawals meet qualifications.

Also known as Qualified ABLE (Achieving a Better Life Experience) programs, these will not only assist you next time you are playing Tax Code Jeopardy but help you create a tax advantaged savings account.

One reason you may not hear much about these tax vehicles is that there really is no way I can discern that advisers can make money on them. But since you and I are members of the same club as tax practitioners, I’m confident you will tell your clients about things that can help regardless of whether there is any profit in it. As my first managing partner the late Herb Cohan used to say, “The world is longer than a day.”

To learn more about future tax-free money, keep reading.

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Employee Retention Credit for the Little People

The Employee Retention Credit (ERC) was probably the ugly step-child of the CARES Act. It received very little attention from tax practitioners, because participation in the Paycheck Protection Program (PPP) precluded ERC. The Taxpayer Certainty and Disaster Tax Relief Act changed all that.

This good news to you as a business owner threatens to overwhelm smaller tax firms, some of which might leave a valuable service to be performed probably less than ideally by the sorts of firms that sell R&D studies and cost segregation. They are already advertising.

To avoid missing out on this valuable service for your client or to capture this free cash for yourself as a small business owner, keep reading.

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Don’t Forget the Cohan Rule but Try Not to Need It

We are creeping up to the centennial of the Cohan rule. Learned Hand’s opinion for the Second Circuit in Cohan v. Commissioner came out on March 3, 1930 . I love this rule so much that I’ve made it the Prime Directive in my own book, Reilly’s Laws of Tax Planning: “If you don’t have documentation, at least have a plausible story.”

However, subsequent legislation, changes in societal expectations, and the passage of time have eroded the usefulness of the Cohan rule for taxpayers. In recent years, there have been more instances of courts refusing to apply it than allowing its use. That’s why in Reilly’s Sixteenth Law of Tax Planning, I advise people to “being right without substantiation can be as bad as being wrong.”

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Charitable Contributions From Your IRA: Tips and Traps

A really neat thing happens when you turn 70 and ½. Your IRAs essentially turn into donor advised funds if you don’t need all the money in them to make ends meet. Rather than withdraw money from your IRA to make charitable contributions, you can make them out of the IRA. So instead of an itemized deduction, you get an exclusion from adjusted gross income. For some people this might be a wash, but for most it probably isn’t. Besides the possibility of not being over the standard deduction threshold, there are a host of computations and thresholds that involve AGI. There are some things you need to watch out for, but first let’s go over the basics.

Segmenting Your Prospects: A Targeted Approach to Business Development

In the accounting field, where client relationships and personalized service are paramount, understanding and segmenting your client base must be a priority. As the accounting landscape evolves and clients diversify, a tailored approach to client segmentation becomes indispensable. Clients are no longer interested in a one-size-fits-all approach to sales and marketing. Therefore, as an accountant and a firm owner, you must adopt a targeted approach tailored to different customer segments’ unique needs and characteristics. In this article, I will delve into the importance of client segmentation within accounting firms and provide insights into implementing this strategy so you can drive growth and enhance your client satisfaction.

10 Ways CTPs Can Use the New Adobe AI Assistant to Analyze PDFs

Launched as a beta in February 2024, the Adobe AI Assistant is a generative AI-powered conversational engine feature within Adobe Acrobat. The app enables you to “chat” with PDF files in natural language and unlock new levels of document productivity.

The AI Assistant can be likened to a knowledgeable librarian for digital documents. Just as a librarian assists you in finding the right books, navigating through complex archives, and answering detailed inquiries about content, the AI Assistant helps users navigate, understand, and extract key information from PDF documents. It provides summaries, clarifies content through answers and suggestions, and links to relevant sections, all designed to make your interaction with digital documents as enriching and efficient as a visit to a well-staffed library.



  • Avoiding Passive Loss Limitations Through Short-term and Alternative Rentals

    Short-term rentals like AirBnb are becoming increasingly popular with taxpayers who invest in real estate. For many taxpayers, the appeal of these properties is the flexibility and cash flow potential. However, there may be an overlooked third tax benefit. In many situations these short-term rentals may not qualify as a rental activity to the IRS, and that may offer a big tax break. While many rental activities generate losses, this can leave taxpayers facing the frustrations of not always getting to deduct those losses right away due to the passive activity limitations.

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    How Business Owners Can Boost Income by Avoiding the $10,000 SALT Cap

    Taxpayers have been whipsawed by confusing rules for the $10,000 limit on deducting state and local taxes (SALT), the most politically charged piece of the Tax Cuts and Jobs Act (TCJA) of 2017. The cap has caused nearly 11 million individuals to lose an annual deduction worth $323 billion. But many owners of private businesses known as passthroughs can avert that financial pain. If you own your company and thus report your business income on your personal federal income tax return, here’s what you need to know.

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    Millions of taxpayers in the United States are using crowdfunding websites like GoFundMe and Kickstarter to raise money for important needs, such as paying medical bills, paying legal fees, or funding a new business venture. Both the IRS and the courts have been surprisingly silent on the tax consequences of crowdfunding platforms. The good news is that established tax law provides a clear road map for answering most tax questions created by raising money from a crowdfunding website. By knowing these rules, taxpayers can use crowdfunding to raise cash and minimize their overall tax exposure.

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    My Client Stuck with a Mistaken C Corporation Election?

    My client formed three limited liability companies (LLCs) to hold his rental properties. Without consulting me, he filed Form 8832, Entity Classification Election, to elect C corporation treatment, effective January 1, 2020, for these LLCs. I want the LLCs to be disregarded entities, which is the most tax-efficient structure for his situation. What is the best way to undo these elections?

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    Quick Guide to Claiming Work-From-Home COVID-19 Expenses to Reduce Your Tax Bill

    This information is particularly important if you are the owner/shareholder of your own corporation – C or S corp. You can set up payroll and designate tax-free reimbursements for you to be working at home – as well other tax-free money for you and for your employees. (We will discuss employees momentarily. Yes, it’s essential.) If being an employee is your main source of income – watch out! The short answer to employees claiming an office in home deduction this year is... There is no deduction!

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    Five Tax Reduction Strategies for the Casual Cryptocurrency Owner

    With so many people looking for more ways to make money outside their 9 to 5 jobs, many are turning to money making methods using technology including trading in cryptocurrency. For tax purposes, the IRS considers cryptocurrencies property, not as currency. Just like other property types, stocks, investments, or real estate, when you sell, swap, or otherwise dispose of your cryptocurrency for more or less than you acquired it for, you incur a tax reporting obligation. As an example, there would be a $1,000 capital gain if 0.1 bitcoin is bought for $2,000 in June of 2020 and then sold for $3,000 two months later. This profit must be reported on the tax return and a certain amount of tax is due on the gain, depending on the tax bracket of the taxpayer. In this example, the gain would be short term requiring the profit to be taxed at the filer’s ordinary tax rate. These rates range anywhere from 0-37%.

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    Extra Taxes on S Corporation Distribution?

    My client plans to take about $15,000 in distributions in excess of his basis from his S corporation construction business. I know this generates tax for him. He’s in the 32 percent tax bracket and single. Does he also have to pay the 3.8 percent net investment income tax and the 0.9 percent additional Medicare tax on this amount? Is there a way for him to avoid taxes on this amount?

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    Reduce Taxable Income Up to $25,000 with Passive Rental Losses

    You have likely heard that owning rental real estate provides great tax benefits. This is true for a multitude of reasons, but there’s one benefit that is arguably the best of the bunch: The Small Taxpayer Allowance for Deducting Passive Rental Losses. Based on average household income levels, more than three-quarters of taxpayers can potentially qualify for this fantastic tax benefit that offers taxable income reduction of up to $25,000.

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