Loopholes

As we prepared our 4th Annual Summer Education Series, our friends at Sandy Bay challenged us to go bigger and do even more live events than we originally planned. So, we did! We are proud to present Think Outside the Tax Box's first ever “Spring Fling” live webinar event. As a monthly or annual subscriber, this webinar is 100% exclusive, and free to you! Every webinar comes with free continuing education credits for those who qualify! Keep reading for more details...

Some new developments arose in March and some new gimmicks. The current hot topics, microcaptive insurers and syndicated conservation easements, remain on the front burner.

February brings us Groundhog Day, but there are always new developments in Tax Court, as well as refreshers to keep practitioners current.

People use the online space to look for love, make business and financial decisions. And all of these decisions can have serious tax implications. That is why as trusted financial and tax advisors, it is important for us to be aware so we can help protect our clients. In 2024, the Federal Trade Commission released a report showing consumers reported losing $4.6 billion in investment scams. That's only the amount reported, so our clients are at risk if they are online making financial decisions. Today, let's look at a newer player in the online investment scam arena: pig butchering. If you're like me, you're probably thinking “what in the world does this have to do with taxes?” Unfortunately, everything. It leads to taxpayers receiving tax bills for money they withdrew but lost as victims of theft.

When we enter upon a new Administration, we wonder at the shape of things to come. But surely since 1916, we have never had an incoming Administration promise us a repeal of the income tax and the reestablishment of the import tariff as the principal source of Federal funding. I would not, however, immediately cease to follow the proceedings of the US Tax Court.

Is student loan forgiveness taxable? Yes. No. Maybe. Sometimes. It primarily depends on the student loan forgiveness program. But like everything else with student loans, there are a number of other factors at play. Why make it easy when you can thoroughly confuse taxpayers, federal student loan servicers and financial planners for years to come? Keep reading to learn when student loan forgiveness might be tax-free and how to prepare your clients for taxable loan forgiveness.

John Anthony Castro is a colorful character. He entered several Republican primaries seeking the Presidential slot after failing to win the primary for a Senate seat representing Texas. He sued to have our once and future President Donald Trump be removed from the ballot on Fourteenth Amendment Section 3 grounds. As we can easily infer, those suits went nowhere. But more than anything, John Anthony Castro was a tax guy with a virtual practice with locations in four cities. Not anymore. Now he is resident in a Bureau of Prisons facility – the Federal Medical Center Fort Worth. On October 30, 2024, Judge Terry Means sentenced Castro to 188 months in prison, followed by one year of supervised release and restitution of $277,243, following his conviction on 33 counts of “Aiding and Assisting in the Preparation and Presentation of a False and Fraudulent Return." Does the sad story of John Anthony Castro hold any lessons for us? Perhaps.

No holiday break for US Tax Court, as fresh developments arise, and some old doctrines need reenforcing. As usual, we've got both common problems and arcana on the radar, with one potential blockbuster.