Loopholes

Something old, something new, is the usual product of Tax Court, and this month is no exception. New: Equitable tolling is applied to out-of-country petitioners (maybe), an abandoned corporate merger escapes Section 1234A capital loss treatment of a break-up fee, the discounted cash flow method of valuation is rejected for valuing conservation easements, and the S.E.C. v. Jarkesy Eighth Amendment controversy continues. Old: Erroneously addressed Notices of Deficiency, witness testifying remotely, sealing witness testimony, CDP is a snapshot, and debt-vs-equity.

A mix of old and new this month, obvious miscues and arcane strategies, an old protester/defier, and the perennial discovery jousts.

College tuition continues to climb, and for many families, financial aid can make or break their ability to afford their child’s higher education dreams. What most don’t realize is that their tax return — filed long before students even begin applying for college — plays a major role in determining how much financial aid they’ll receive. This is where you come in. Tax professionals and financial planners are uniquely positioned to help clients qualify for more college financial aid. But only if you know what to look for.

Once again, Tax Court provides slices of life as well as hyper-technical drilldowns into convoluted legal conundrums. To any who say that tax law is dull, I refer them to the annals of 400 Second Street, NW, where anything goes.

We are thrilled to bring you the 2025 Summer Education Series, sponsored by Vistia! All summer long we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax. Each webinar will feature our usual blend of high-quality education and entertainment and include continuing education credits for those who qualify. All of this is included in your regular subscription! Continue reading to see what we have in store...

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.