About this episode

Eliot Thomas and Amanda Wynalda discuss various tax strategies related to real estate, including the use of 1031 exchanges and capital gains mitigation for rental properties.

In this episode of Tax Tuesday, Anderson attorneys Eliot Thomas, Esq., and Amanda Wynalda, Esq., tackle ten listener questions covering a range of real estate and tax topics. They explain when short-term rentals belong on Schedule E versus Schedule C, and how material participation and substantial services factor into that decision. They explore strategies for mitigating capital gains on rental properties, including 1031 exchanges, Delaware Statutory Trusts, and UPREITs, and clarify why house flippers cannot use a 1031 exchange since flipped properties are treated as inventory. Eliot and Amanda also cover write-off strategies for fix-and-flip investors using a C corporation, grouping rental activity with an operating business to offset income, and deducting stock trading education expenses through startup costs. Additional topics include accountable plans for home office and mileage reimbursements, the difference between contributing funds to a for-profit business versus donating to a nonprofit, reporting the sale of foreign property on a U.S. tax return, and whether a prior-year cost segregation study can still be applied in 2026. Tune in for expert, practical guidance on all of…

Topics covered

• 1031 exchange
• flipping houses
• Schedule E
• Schedule C
• capital gains
• Delaware Statutory Trusts
• UPREITs
• C corporation
• accountable plans
• foreign property

Keywords

• real estate
• tax strategies
• short-term rentals
• material participation
• fix-and-flip investors

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• How To Sell 1031 Replacement Properties Without Tax Penalties · March 10, 2026 · 1h 2m
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