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Tax Tuesdays
How to Decrease Taxes When Selling a Rental Property

Welcome to Episode 197 of the Tax Tuesday show. Host Eliot Thomas, Esq., and Kurt Bergfjord, CPA help answer your questions. We send a big thank you to all our people online answering your questions today.

Today Kurt and Eliot answer listener questions on tax liens and wholesaling. They discuss the complexities of property tax implications, the benefits of a C-Corp for property flipping, and the tax implications of inheritance. The episode also answers inquiries about home office expenses, the intricacies of short-term rentals in real estate, and running an active business in a retirement account.

If you have a tax-related question for us, submit it to taxtuesday@andersonadvisors.


  • “Are there any tax implications for wholesaling and tax liens?” – Yes, tax liens can lead to property auctions, affecting real estate investment strategies.
  • “When I pass on and leave property to my children, are there estate taxes?” – right now estate exemption for a couple is 25 Million dollars. Better to let them inherit than to gift it to them…
  • “I own properties in two states… any restrictions on travel deductions?” – The IRS would say as long as your trip is more than 50% business days, your travel is 100% deductible.
  • “We have 8 properties to sell, no longer want to be landlords…but we want cash flow” – Calculate the capital gains…pay or defer, use a 721 exchange to turn rentals into units in an investment trust, which provides more stable cash flow and hands off investments.
  • “What is the right way to deduct my personal residency expenses, such as mortgage interest, mortgage insurance, real estate taxes, homeowners insurance, depreciation, so on and so forth? How do I do that? Through an accountable plan as an employee of my corporation, or do I do that tax time on my personal return?” – An accountable plan requires a separate dedicated office space/room in your home…
  • “I own a single member disregarded LLC, which in turn owns a rental property. The rental property provides me with tax Tax deduction, mainly because of depreciation. If I were to take the property out of the LLC as an owner-drawer distribution, would I be liable for any capital gains tax or depreciation recapture?” – In this circumstance, if you’re just pulling it out of an LLC that you own, that is disregarding to you, is not really considered a sale for the IRS purposes.
  • “When you pay your kids, may that payment come from your personal bank account?” – Generally, it’s advisable to pay from a business account for clarity and separation.
  • “If I use a Sidra self-directed IRA to purchase short-term rental property, does that qualify for me as a real estate professional?” If I use the Sidra self-directed IRA funds plus a mortgage to buy a rental property, once the mortgage is paid off, is the whole property considered property of the IRA?” – No, activities in a retirement account don’t qualify towards real estate professional status. If the IRA funded the purchase, the property belongs to the IRA.
  • “What are the requirements to have a second home be considered a short-term rental? Will I be able to expense furnishing costs and other expenses? Also, how does cost segregation work in this situation? – If you’re going to be using any property for more than 14 days or 10 percent of the fair market rental days out there one you have to allocate the expenses associated with the property between personal time and business time.
  • “I formed my two LLCs last year but haven’t funded them or used them in any way. I missed the tax return filing deadline this spring. Now what? File the returns and beg forgiveness to not have to pay late fees, close the business down, start over? So I got some LLCs set up not telling you anything about those LLCs, kurt, but I will tell you that I didn’t file the returns. What am I going to do?” – How are these LLCs taxed? Knowing that answer will be the first step in determining what you need to do with your LLCs.


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Full Episode Transcript: 

Eliot: Good afternoon, everybody. Welcome to Tax Tuesday. My name is Eliot Thomas. I’m Manager of the Tax Advisors here at Anderson filling in for Mr. Toby Mathis, who is away right now. I’m joined by our CPA extraordinaire, Kurt Bergfjord. Say hello, Kurt.

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