August 05, 2025

Capital Losses Explained: When to Write Off a Losing Investment

59 minutes

Today on Tax Tuesday, Anderson Advisors Barley Bowler, CPA, and Eliot Thomas, Esq., focus on capital gains, cryptocurrency, stock trading structures, and real estate strategies. They explain how capital losses are deducted and the $3,000 annual limit that hasn't been adjusted for inflation since the 1950s. You’ll hear about Bitcoin's tax treatment as a personal asset with favorable capital gains rates but note the lack of wash sale rule protections. They demonstrate how a trading partnership with a C corporation can provide significant tax advantages through accountable plan reimbursements. The episode extensively covers real estate topics including the distinction between repairs and capital improvements, the inability to deduct lost rent from deadbeat tenants, and home office deductions for primary residences. They explain 1031 exchanges in detail and explore strategies for managing large capital gains from personal residence sales, including converting to rental properties and the Section 121 exclusion benefits.

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Highlights/Topics:

"I have a large capital loss. How are capital losses deducted? When should I consider taking a tax write off by closing the position, unrealized versus realized gains?" - Capital losses offset gains first, then $3,000 annually against ordinary income.

"My wife and I are considering investing in Bitcoin. What are the tax advantages or disadvantages of doing so investing crypto for crypto for that type of investment?" - Bitcoin treated as capital asset with favorable rates, no wash sale rules.

"I do a lot of stock buying and selling. Is it tax efficient to set up a business entity?" - Trading partnerships with C corporations provide excellent accountable plan reimbursement opportunities.

"Can you explain what differentiates whether a real estate rental deduction would be categorized as a maintenance repair deduction versus a capital expense deduction? And provide examples. Please explain how these are treated differently from a tax perspective as well." - Repairs maintain property condition; capital improvements add value, extend life, or change use.

"Can I deduct lost rent from a deadbeat tenant?" - No deduction available; you simply don't report income you never received.

"I've heard you talk about renovations major to rental property and tax advantages, but what about for my primary residence? I need to finish the basement. Upgrade the house. This is also the address of my C corp business is registered to, and I operate a home office out of it. When I complete taxes next year, is there anything specific that I can take advantage of due to this large expense?" - Primary residence improvements add to basis; home office allows business-related deductions.

"Can I do a 1031 exchange on real property?" - Yes, but not on primary residences or inventory properties like flips.

"I bought a rental property in California in 2019 for 700,000 as replacement property from a 1031 exchange. 400,000 was from the sale of rental property in Seattle, Washington. 300,000 from my savings. I took a loan, also a 600,000 for expansion, uh, in repairs in January of 25. How much of the money I invested from my personal savings, the 300,000, can I get back without having to pay tax? I listed my rental property for 935,000." - Any cash taken from 1031 exchange creates taxable boot; consider real estate professional strategies.

"I'm selling my personal residence next year. We currently have an anticipated capital gain of a million. I'll be paying taxes on 500,000 of the capital gain above the capital gain exclusion for married filing joint. What tax strategy would you suggest that I may plan to use in order to mitigate paying federal taxes against the 500K capital gains? Could I do a 1031 exchange or of a personal residence? Can we convert the personal residence to a rental and then sell it in one to two years?" - Use Section 121 exclusion first, consider converting to rental within five-year window for 1031.

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