Guest Article

In the realm of tax research, the journey from traditional methods to the digital age has been transformative. The evolution of AI in this field marks a significant milestone, reshaping how tax professionals approach complex regulations and compliance. This journey began with simple tax software, gradually advancing to more sophisticated AI tools capable of analyzing large datasets and identifying patterns beyond human capability. Today, we stand at a pivotal moment where AI, particularly ChatGPT, is not just an aid but a game-changer in tax research. Enter "BEST WILD", a revolutionary technique designed specifically for this new era. By integrating the advanced capabilities of ChatGPT, "BEST WILD" offers a systematic approach that transcends traditional boundaries in tax law analysis. This method doesn’t just aid in navigating the complexities of tax regulations; it revolutionizes the process, making it more efficient, accurate, and insightful.

Various rulings and tax agency actions in 2023 were arguably “unusual” and “surprising.” Most of these items were not the key holding of court decisions or IRS news releases or guidance. They were more subtle or buried. This article uncovers a variety of these oddities and posits what we might learn from them.

Wolfgang Frederick Kraske, representing himself in Tax Court, pulled off a rare feat. He managed to get two opinions for the price of one in a relatively low stakes case . My friend Lew Taishoff found the regular decision about the $4,574 Section 6662(a) accuracy related penalty to be of great interest . I think the more interesting story is in the memo opinion that covers the tax deficiency of $22,687 for the years 2011 and 2012. It is mostly about Section 183: Activities not engaged in for profit, commonly referred to as the hobby loss rule. Although in this case, the activity does not even seem to get up to the level of a hobby, much less a business conducted for profit. I didn’t dig any deeper into the case, so the story you are getting is what Judge John H. Gale concluded. Kraske might have had something to say if I had interviewed him.

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.

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.

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.