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.

Time flies when you’re dealing with taxes. For instance, eight years must have seemed like an epoch when Washington passed the Tax Cuts and Jobs Act of 2017 (TCJA), the biggest federal tax reform in decades and one that altered tax brackets, deductions, and estate planning, to name just a few. Best of all, lawmakers probably thought back then, we won’t have to worry about some of these provisions changing until all the way off in 2026! Except suddenly, we now have less than 26 months to get ready for the end of nearly two dozen TCJA provisions that will happen without action from Congress. That’s barely enough time for some of the planning before what could be one of the biggest groundswell tax years of recent memory.

When I started my business, referrals and testimonials were not on my mind. Like most entrepreneurs, my crucial motivator was to have freedom of time for my family, to expand my skill set, and to remove the cap on my earnings potential. When I got my first client as a side hustle, my referral source was a board member who knew my skills very well and recommended me to the non-profit he served as treasurer. In December 2018, a prospect asked me for referrals, and I had no idea what to say. There was only a little besides my resume and employer as a reference. Then I thought, hey, I have my non-profit client, and I asked my client whether they would speak with this prospect and answer any questions they had, and they agreed. That’s when I realized the power of referrals and testimonials.

Considering how soon Halloween comes after October 15, the extended due date for individual returns, having a tax horror story seems really appropriate. The horror story came out on October 24, with the Eleventh Circuit decision in the case of Lee v U.S. Dr. Wayne Lee seemed to have done everything right to be in compliance. His estimates overpaid his taxes every year, and he would let the refund ride into the next year. He hired a CPA to prepare his returns and dutifully signed and sent the CPA Form 8879 IRS e-file Signature Authorization. He did this for his 2014, 2015, 2016, and 2017 returns. Then disaster struck.

The last month of 2023 featured more technical expositions than policy discussion. Practitioners will find insights worth their time. Generalists shouldn't overlook some nuggets here. As always, Tax Court sees and deals with more varieties of income taxation than any other court.