You’re tax professionals. You don’t need me to tell you that the money you are going to win in the virtual office pool on “the big game” is taxable income. You also don’t need me to tell you can’t net your winnings with the cost of the wager. You don’t, right? Most of the rules for reporting gambling income and deducting gambling losses for individuals are well understood with the possible exception of the session rules for slot machine play. I’m not going there—well, not in this article. This article is going to explore the nuances of tax optimization for people who have decided to go all in and turn their leisure time activities into a job.
Tax Research in an AI World
Keith Schroeder, EA
It has never been harder to do quality tax research than at any time in my 43-year career in tax accounting. In the 1980s, when I was part-time in the industry, there was no internet. Since I was part-time, I ordered Publications 1132, 17, and 334. The rest I found at the library. A few hearty souls might even remember when the post office had stacks of tax forms for the public. Once I went full-time for the 1989 tax season I needed more resources. CCH was my tool of choice. I still used IRS publications and the library. My handy reference guide of choice was, and still is, the QuickFinder. I never used TaxBook much, but it is another good resource for general answers. Then came the internet. The promise was that we would have the world at our fingertips. And for the large part we did, only we forgot some things we would rather keep at an arm’s length. The internet slowly allowed us to replace rooms in our office filled with tax guides and forms with online resources. Law offices and accounting firms often wrote tax articles on narrow tax subjects. Research was easier than ever.
Then came AI.
