Loopholes

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!

Since at least 2001, the IRS has issued annual news releases warning taxpayers of scams they should be aware of and stay clear of. The release in 2001 included just eight scams but starting in 2002, the IRS expanded the list and dubbed these scams with the catchy moniker: the “Dirty Dozen.” In describing these lists, the IRS often warns taxpayers to “remain vigilant” against the scams, to not “fall prey” to them, and to “be on the lookout for” these dangerous activities. While the warnings seem to be directed to individual taxpayers, the lists sometimes include warnings of scams directed at return preparers and employers. Tax practitioners certainly need to be aware of these scams to exercise appropriate due diligence to know if any client is involved in a scam such as an abusive tax shelter, and to help educate clients about the numerous and growing number of scams many of which are designed to steal their personal and financial data and resources. This article covers the 2022 “Dirty Dozen” list. It also includes suggestions on how practitioners might use this information in tax compliance and planning and to help clients protect their identities and assets and avoid tax problems. Additional resources for dealing with the items on the list are provided. A chart listing the “Dirty Dozen” items from the start in 2001 through 2022 is included to show trends and the reality that some scams such as identity theft, phishing, return preparer fraud and frivolous tax arguments have made the list almost every year. Click here to continue reading.

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.

Far too many of these Employee Retention Credit (ERC) claims are nonsense. Now don’t get me wrong. I enjoy helping businesses claim the ERC. I have written in these pages about the unique ways a business may qualify and how to use startup eligibility even for existing employers. But let’s be honest: People are manipulating this program beyond belief. The refund dollars are too attractive and have created far too large an incentive for shops charging high commission fees (I have seen fees charged between 10 to 35 percent of the refund). In the coming years, numerous aggressive ERC shops may contact you if they haven’t already. How do you know whether a claim is legitimate or nonsense? Here, we will review the most prevalent bad arguments to help you avoid trouble.

Question: How much time should be devoted to studying tax planning? Can’t I just select a software providing Artificial Intelligence to Inform Me What to Do? Answer: To answer this question Dear Reader, I’ll ask a question in response. Are you a user of TurboTax or a similar software tool? Chances are as a reader of Think Outside the Tax Box, you use something (or someone) different than software purchased at a big box store. The answer to this question may be a similar situation to a semi-regular TikTok viewer of DIY household construction projects. Does the job require a router or a Dremel tool? If you’ve heard me talk about tax planning before, no doubt you’ve heard me describe tax planning software as an instrumental tool. It can provide valuable insights such as data extracted from your tax returns, calculation of minimum required estimated tax payments, and even a few tips to save annual tax. Whether you are a do-it-yourselfer braving a construction project in your home or a new business owner or novice tax planner, the answer depends on the nature of the job you are doing. Is it possible for this experienced Tax Planner of more than 20 years with an advanced degree and thousands of tax plans to complete a bathroom remodel in just a weekend with a Dremel tool? Certainly. I’ve even got the pictures to prove it. Just like the bathroom-in-a-weekend, it is possible with an off-the-internet-software to develop a few ideas to save some tax dollars. But if you look closely at my personal photos – you’ll notice the glue expired on my “driftwood” mirror frame. The recycled wood tiles failed to stay up with the shower moisture in the air, and while the dimensions of my replacement countertop – the walls were just a hair too uneven in my old house. In the end, my weekend project took more than 4 weekends of my precious free time, more than $1,200 in the after-the-fact hired help to fix my handywork, and a little of my pride revealing this online to a public audience. To read about when it is a DEAL BREAKER to rely on AI tax planning software, click here to continue reading.

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!

A frequent question for tax pros is, “Can I put my primary residence in an LLC?” It is well known that owners holding rental real estate in a limited liability company want to ensure they’re receiving all their entitled benefits. The problem is, simply placing a personal residence in an LLC does not change the fact that the residence is for personal use and not for business. If you’re hoping that using an LLC will help you gain tax advantages, the LLC might not be the right choice for the property. The main purpose of an LLC is asset protection. Aside from this valuable benefit, many choose an LLC to hold their business activity. However, simply using an LLC for anything personal not only doesn’t provide additional tax benefits, but it may also cost you the available benefits for your home. If, however, you’re thinking of locking in the tax advantages you currently have while converting your home to a rental, consider selling it to an entity you own before you make it available for rent. To learn how to avoid losing tax breaks and gaining more, keep reading.

Question: I have a fully depreciated rental property that I purchased more than 40 years ago. What are some tax planning strategies I should consider? Answer: Congratulations! You defied the odds and the thousands of advertisements claiming that real estate investing is an easy way to get rich. But now that your precious “paper losses” a.k.a. depreciation is long gone, it’s time to search for a new way to create tax advantaged income. There are some fun ways to “re-depreciate” your investment again, and even put some of those carryovers to use. But before jumping into tax, let’s also consider your investment returns since you achieved this milestone. One issue I see many real estate investors face is that they tend to be short-sighted with their goals. You might, initially, have a goal to get rental income sufficient to cover your mortgage payments. You might have a longer-term goal of eventually having rental income pay off your mortgage. Often, when either of these events occur, I notice some investors sit back to enjoy their success. While success specifically means something different for everyone, from a wealth and tax perspective it is important to also evaluate your choices and returns on your investment. Examining the cash-on-cash return on investment is especially important for real estate investors who may not consider more than their initial down payment as their own investment. In addition, identifying loopholes which allow you to re-depreciate your property can also create significant tax benefits you cannot afford to miss. Keep reading to learn more…