In this Tax Tuesday episode, Anderson Advisors' Barley Bowler, CPA, and Eliot Thomas, Esq., answer listener questions covering entity structuring, real estate tax planning, investing, and charitable giving strategies. They explain when it makes sense to form an LLC or S Corporation for a real estate flipping business and whether new investors should wait until after closing their first deal. They also discuss how profits earned inside an LLC trading stocks and stock options are taxed, and whether leaving funds in a brokerage account changes the tax treatment.

Barley and Eliot break down whether a cost segregation study makes sense for a long-held commercial property undergoing significant capital improvements, and how that decision compares to selling the property, completing a 1031 exchange, and performing a cost segregation study on replacement assets. They also explore tax-efficient charitable giving strategies, including ways to contribute appreciated assets or funds designated for charity while minimizing capital gains taxes. Tune in for practical guidance on these tax-saving strategies and more!

Submit your tax question to taxtuesday@andersonadvisors.com

Resources

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Chapters:

0:00 Intro

9:32 Please speak about vacation rentals that are considered primary residences. We will rent our new property out in the summer months while we are at our secondary residence and stay there in the winter months (so we can’t take advantage of the STR loophole). What tax strategies are available to us in the above case?

17:03 We are selling our company at the end of July 2026. Usually this would be treated as long-term capital gain (taxed at 23.8%) but because I haven't been with the company for 12 months, I believe I would be taxed as ordinary income. Could I invest those funds in a Qualified Opportunity Zone to avoid paying ordinary taxes? Are there new rules with OBBBA that will take effect January 1, 2027?

27:03 I have a C Corporation that earns income from management fees normally paid annually from the LLCs the C Corp manages. During the last C Corp fiscal year, no management fees were paid due to the LLC not having income. Does the C Corp still need to file a tax return if it has no income, and does this mean the C Corp cannot pay any reimbursements for this tax year?

31:45 Please explain the details of when you sell a stock at a loss and repurchase the same stock within 30 days. (Wash Sale Rules)

35:57 At what point do I need to form an LLC or S-Corp for my real estate flipping business? I am just starting in the market and was told not to worry about it until I made my first deal. Is that true?

39:45 I have an LLC for trading stock options and stocks. If I make $1,000,000 profit and do not transfer it out of my brokerage account to me personally, is this money taxed, or is it taxed when I do pull it out of the account?

45:15 I am the managing partner of a general partnership that owns a strip center for many years with little depreciation left. We are spending about $500,000 on a new roof and paving to put a big-box tenant in a long-standing vacancy. Would a cost segregation study benefit here? Should we sell (at a massive profit) and 1031 into new assets and then do the CSS?

51:09 Is there a way to put funds into an account for charity and it not be taxed on gains?

57:23 Can you please explain the non-AFS 417(c) method? Can it be used for an LLC partnership? And can it be used to create a loss, or does the loss carry over to the following tax year?