In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., tackle listener questions on reducing capital gains taxes and advanced tax strategies for real estate investors and business owners. They explore the intricacies of cost segregation studies and bonus depreciation versus Section 179, including timing issues for renovations. Amanda and Eliot discuss strategies for minimizing capital gains after decades of depreciation, converting ordinary income to capital gains in development deals, and the tax implications of oil and gas working interest investments. The duo also covers deductible expenses for corporate retreats, entity structuring for piano tuning and bookkeeping businesses, and sophisticated trading partnerships using C corporations. Finally, they take a deep dive into Solo 401(k) contribution limits, explaining the differences between employee contributions, employer matches, and the mega backdoor Roth strategy for maximizing retirement savings. Tune in for expert advice on these and more!

Submit your tax question to taxtuesday@andersonadvisors.com

Highlights/Topics:

"I purchased a rental and did a cost seg in 2024. I renovated it in 2025. Can I use a cost segregation and/or Section 179 to depreciate the new renovation assets in 2025?" Answer: Yes, bonus depreciation works; 179 has limitations.
[21:16] “How can I reduce capital gains on the sale of a rental property after nearly 27 and a half years? The accelerated depreciation reduced the basis to zero." Answer: 1031 exchange, installment sale, or opportunity zones.
"How can I get capital gains on my K-1 instead of ordinary income on my investment into a real estate developer corporation?" Answer: Development corporations typically generate ordinary income, not capital.
"What expenses for an off-site retreat for an LLC member and officers meeting are deductible? For example, travel, lodging, meals, activities." Answer: Travel, lodging, 50% meals if genuinely business-related.
"If I invest in an oil and gas working interest and I have a first year larger intangible drilling cost loss than is needed for a given tax year based on adjusted gross income, can the excess be carried forward to a future tax year as a net operating loss? Would the NOL have alternative minimum tax implications as well?" Answer: Yes, NOL carries forward; minimal AMT concerns today.
"How do I set up a holding company in California? I want the holding company to own my two companies. One's a piano tuning business and then a bookkeeping business. I have an average income of $125,000 per year combined: $45K for piano, $80K for bookkeeping." Answer: Wyoming LLC holding company owns two California entities.
"I want more information on how I can structure my LLC more efficiently for day trading. What can I do to minimize my taxes for the new year? How can I lower my capital gains tax from day trading?" Answer: Trading partnership with C corporation for deductions.
"Please take a deep dive into Solo 401(k) contributions. What are the individual contribution limits, employer match limits, and especially the voluntary after tax contribution limits. Which components need to be earned income and how does this change if contributing to a Roth 401(k)?" Answer: $72K total; $24.5K employee; mega backdoor uses after-tax.

Resources:

Tax and Asset Protection Events

https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=how-to-reduce-capital-gains-taxes-when-selling-a-rental-property&utm_medium=podcast

Schedule Your FREE Consultation

https://andersonadvisors.com/strategy-session/?utm_source=how-to-reduce-capital-gains-taxes-when-selling-a-rental-property&utm_medium=podcast

Anderson Advisors

https://andersonadvisors.com/

Toby Mathis YouTube

https://www.youtube.com/@TobyMathis

Toby Mathis TikTok

https://www.tiktok.com/@tobymathisesq

Clint Coons YouTube

https://www.youtube.com/@ClintCoons