Main Street Business #607 Open Forum — Tax Expert Answers Your Most Difficult Tax & Legal Questions!
7 snips
Jan 30, 2026 Tough tax and legal questions get clear treatment with topics like selling high-value collectibles and why entity choice does not erase capital gains. Listeners hear about charitable remainder unitrusts, depreciation rules, and when trusts are worth the cost. Practical S‑Corp effects on FICA and Social Security, self-rental real estate strategies, and prohibited transaction pitfalls in IRAs and Solo 401(k)s are also covered.
AI Snips
Chapters
Transcript
Episode notes
Sell Collectibles Through A CRUT
- Use a Charitable Remainder Unitrust (CRUT) to avoid immediate tax on high-value collectibles and retain control of investments.
- Donate the item to a CRUT, receive a partial deduction, get annual payouts, and avoid the 28% collectible tax plus state tax on the sale proceeds.
Offset Gains With Depreciable Investments
- Offset a large taxable gain by reinvesting into assets that generate immediate deductions like depreciable real estate or oil and gas IDC.
- Consider short-term rentals, oil & gas investments, or the 2027 Opportunity Zone rules to defer or reduce tax on the sale.
Don't Buy Trust Hype Blindly
- Avoid expensive irrevocable self-settled trusts unless you truly give up control and understand the baggage.
- Use a revocable living trust for probate avoidance or consider a domestic asset protection trust only after careful legal review.