In this Tax Tuesday replay, Anderson Business Advisors’ Barley Bowler, CPA, and Eliot Thomas, Esq. answer real-world tax questions on Roth IRA conversions, investing in real estate with retirement accounts, and depreciation after a 1031 exchange.
How can you estimate the tax impact of a Roth IRA conversion before filing your 2026 tax return? Is buying real estate through an HSA, traditional IRA, or Roth IRA a smart investment strategy—and what tax rules, advantages, and potential pitfalls should you understand before moving forward? Plus, how is depreciation calculated after a §1031 exchange when you sell a rental property and acquire a replacement property?
Barley and Eliot break down these questions and explain the tax considerations investors and business owners should keep in mind when planning their next move.
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Show Notes:
0:00 Intro
9:05 When I convert a Roth IRA this year how do I determine the accurate tax impact from the conversion amount before filing the 2026 tax return?
20:18 Is it a good idea to buy real estate using your HSA, IRA, or Roth IRA accounts? What are some pros and cons and how should I proceed?
35:51 How is depreciation calculated going forward after a §1031 exchange following the sale of a rental property and purchase of a new one?
43:41 I am planning to use a HELOC from my personal residence and use the funds for my trading activity. Can I deduct the interest as investment interest under Form 4952 if I loan the money to my LLC, and what counts as “net investment income”?
1:04:05 I will have a tax loss carryforward if I elect to use Section 475(f) mark-to-market accounting method. What types of income can I offset?
1:08:51 I currently have a Living Trust that ABA set up in Wyoming, as well as an LLC. I put all my cryptocurrencies into the LLC. Is this the best way to mitigate my taxes? I paid about $2.00 per share and the value is growing substantially. What other options might be better than the LLC?
1:12:42 Is there a way to organize and structure an entity to trade a taxable account and be able to defer taxes until a cash withdrawal?
