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

AUTHOR SPOTLIGHT

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 Forbes.com 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.

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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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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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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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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 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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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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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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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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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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Does the Cohan Rule Still Matter?

Looking to write off your favorite wine? Better yet, how about deducting it while lacking the receipts?

For nearly a century, freewheeling salespeople, hobnobbers, and schmoozers alike have treated potential customers and employees to fine dining and entertaining all while seeking the maximum tax break in the process with minimal substantiation.

While proving these expenses has certainly gotten easier with technology, smart planners have made use of the so-called Cohan rule to enjoy the deductions without the paperwork nightmare. Want to make use of it yourself? Read on to learn more.

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Conservations Easement - Good Execution is the Key

Conservation Easements: Good Execution Is the Key

If someone approaches your client offering four to one deductions on conservation easements (probably somewhere in the Southeast), you need to do your best to talk them out of it. And if you cannot, it may be best to let some other practitioner have the honor of preparing their return.

On the other hand, if your client has land or a building they would like to preserve forever, a conservation easement may be just the thing. Assuming the desire to have the property preserved anyway, it is about as close to a free lunch as you can get. Good execution is the key to making it work. Read on to learn how!

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Keeping Your Records

Cecile Barker and Why You Need to Keep Records Longer Than You Thought

Cecile Barker has bad news from the Eleventh Circuit. They have upheld the Tax Court’s disallowance of his multi-million dollar net operating loss deduction (NOL) largely generated by SoBe Entertainment LLC. SoBe Entertainment is a record label that has represented numerous artists included Brooke Hogan, daughter of Hulk Hogan. The indirect Hulk Hogan connection makes Mr. Barker a tangential figure in a fascinating story you can read about in Conspiracy – Peter Thiel, Hulk Hogan, Gawker and the Anatomy of Intrigue by Ryan Holiday. For purposes of this article, we will stick to the tax story which began with a Tax Court opinion in 2018, which I covered previously.

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Bob Dylan Shows How to Beat an Imminent Tax Increase

Timing might be one of the oldest, most valuable tax strategies known. Essentially, a timing strategy allows a taxpayer to pay tax when rates are generally lower rather than when in a higher tax bracket or when facing increasing tax rates. Given this, 2020 may have been an optimal time to sell capital assets if tax rates rise under the new administration.

President-elect Joe Biden has suggested taxing capital gains as ordinary income for high-income taxpayers (more than $400,000), as well as raising the top tax rate from 37% to 39.6%. Here’s how to cash in on the lower rates and, more importantly, when. While tax law changes seldom pass quickly, we often see changes made retroactive to the beginning of the year they are voted into law.

Based on a recent story in The New York Times, Bob Dylan may have anticipated the increase when he sold the copyrights to his catalog of more than 600 songs for $300 million. Not to fret if you found yourself missing the beat of Dylan’s lead, there are many things a taxpayer can do to reduce capital gains tax, especially for self-created works of art. Here’s how.

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Be More Aggressive in Claiming “Hobby Losses”

Imagine your clients, a couple, tell you they are going to start a business. They will breed horses, start a band, get into car racing, or write a book about beekeeping. Of course, there will be losses starting out, but they have plenty of income to shelter and in the long run, they figure they can make money.

If you are as I used to be, you may discourage them from deducting the losses, particularly if there are other complications on their return. You figure the Schedule C or Schedule F will be a red flag, and they will likely lose on audit. I’d like to suggest that you rethink that attitude.

It is fine if you want to talk your physician client out of going into horse breeding or raising cattle, but if they are going to do it anyway, you should not try to talk them out of claiming the losses. Rather, you should talk to them about what they need to do to beef up their chances of winning an audit of their cattle ranch. And the great thing is that you are the one who can help them more than anybody. Read on to find out how.

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Airline Miles, Other Reward Programs, and Taxes – What You Need to Know

Frequent flyer miles and similar programs for other forms of consumption like grocery shopping raise a host of tax issues. There are the concerns of the recipients of the “rewards” and also of the issuers of the various sorts of points. A recent Tax Court decision brought the taxability of rewards into focus again and the opinion encourages the IRS to provide more guidance. Here is where we seem to be now.
This is the first of two articles discussing the tax strategies available to boat owners. Part 1 focuses on using a boat as a residence, but if that doesn’t meet your needs, stay tuned because Part 2 will cover boats for business use (including as a home office). Why not consider both options and see how your tax savings can help fund your floating condo? Keep reading to learn more.

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CURRENT EDITION

‘Tis Still the Season to Be Giving

It is the best of times, it is the worst of times – and charity cannot only help those in need; it can provide some hefty tax deductions to the donor, as well.

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.

Don’t Overpay Tax on Crypto Forks and Airdrops

Practically overnight, cryptocurrency has gone mainstream, with more and more investors funneling money into Bitcoin, Dogecoin, and other cryptocurrencies. The IRS has responded with increased interest and scrutiny, demonstrated by the addition of the cryptocurrency question on the front page of 1040.

Whether you have invested in cryptocurrency or not, you are required to answer this tax return question. Many investors choose to take the most conservative position to avoid future correspondence from the IRS but trying to avoid a letter is no reason to pay more tax than necessary.

Keep reading to learn more!

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  • 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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    GOFUNDME & KICKSTARTER: TAXABLE? DEDUCTIBLE?

    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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