A retired airline pilot took advantage of a “fly for free” fringe benefit, providing relatives with free airline tickets. Those relatives didn’t include the value of those tickets in income on their 2016 tax returns, and the IRS issued a notice of deficiency. The ensuing disagreement hinged on one question: Who is an “employee” under the meaning of Section 132(h)? This case study is part of a Self-Study Video Course available from Western CPE that can be purchased for CPE credit. Visit https://wcpe.co/podcast to get started.

A Virginia-based S corporation specializing in agriculture and horse-breeding transferred land to various third parties. Some of these transfers were made gratuitously, and the others were reported as nontaxable loans with accompanying re-purchasing agreements. The IRS determined that not everything was as it seemed, arguing that the taxpayers owed millions. But what did the US Tax Court conclude? Tony and Damien dig in. This case study is part of a Self-Study Video Course available from Western CPE that can be purchased for CPE credit. Visit https://wcpe.co/podcast to get started.

After a real estate venture turned sour due to legal disputes and the 2007 real estate market crash, William Musselwhite sold several lots of land for a major loss. His case posed the question: Did those losses qualify as an ordinary loss or a capital loss? In this episode, Tony and Damien discuss the legal issue at the core of the dispute. This case study is part of a Self-Study Video Course available from Western CPE that can be purchased for CPE credit. Visit https://wcpe.co/podcast to get started.

A couple bought a home, then eventually filed for bankruptcy. After CitiMortgage short sold the home, the taxpayers claimed a mortgage interest tax deduction. The IRS disallowed it, but the 9th Circuit Court disagreed. In this episode, Tony and Damien discuss why. This case study is part of a Self-Study Video Course available from Western CPE that can be purchased for CPE credit. Visit https://wcpe.co/podcast to get started.

When is rental income subject to Self-Employment Tax? What if you rent out a room in your own home? What if you provided amenities like maid service, Wi-Fi, or beachfront access? Where is the line drawn? Tony and Damien discuss IRS Chief Counsel  Memo 202151005, which sought to answer the question for taxpayers and their advisors. This case study is part of a Self-Study Video Course available from Western CPE that can be purchased for CPE credit. Visit https://wcpe.co/podcast to get started.

The "Significant Participation Activities Test" and "Five of Ten Years Test" are used to determine if a taxpayer materially participates in an activity. The question considered in TAM 202229036 is this: Does participation via the SPA rule count for purposes of the "Five of Ten Years" test? The results might surprise you. In this episode, Tony and Damien break down the IRS's analysis, as well as what it means for taxpayers. This case study is part of a Self-Study Video Course available from Western CPE that can be purchased for CPE credit. Visit https://wcpe.co/podcast to get started.