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Anderson Business Advisors Podcast
What Is The Best Tax Efficient Way To Purchase An Existing Business?

Welcome to another Tax Tuesday episode of the Anderson Business Advisors podcast. Today, attorneys Toby Mathis, Esq., and Eliot Thomas, Esq., explain tax strategies for listener-submitted questions. The conversation digs into S-Corp vs. C-Corp for property management, understanding Unrelated Business Income Tax (UBIT) for non-profits, qualifying for Real Estate Professional status, and cost segregation and bonus depreciation for rentals.
Submit your tax question to taxtuesday@andersonadvisors.


  • “Is it better to have an S-corporation or C-corporation as your property management company managing your land trust and property held in your disregarded LLC? Are you required to have payroll with the S-corporation?” – With the management corporation, S or C, I personally like the C-corporation better.
  • “Where and when does UBIT apply to real estate investing and generally to alternative investments? – You’re going to run into this when you have exempt groups or we’ll call them entities, nonprofits are also exempt.
  • Does an accountable plan have identical benefits when comparing a C-corporation versus an S-corporation for a new business?” – being a new business or not shouldn’t change too much. It’s just a C Corp versus S Corp.
  • “How do you know how much you can convert into a Roth IRA from a traditional one without getting pushed into a higher tax bracket when you don’t know what your investment gains will be?” – we don’t look at the taxable gains – whatever your tax bracket is, that’s what’s going to determine.
  • “Augusta rule. I am my own real estate broker office scene out of my home. I just hosted a large client appreciation party at my house using rooms in a garden that are not my office. Can I apply an Augusta rule to it? If yes, could applying the Augusta rule increase my chances for an audit and to what percentage? – Augusta rule is 288. You can rent out your home up to 14 times a calendar year. This is entertainment, you could maybe deduct 50%, I wouldn’t use Augusta for anything entertainment.
  • “My question is I’ve never been able to take real estate professional status due to full-time employment as a W-2 employee. I took early retirement on January 2nd of 2024 of this year. I am still being paid the remainder of 2024 biweekly, but not actually working. I’m a licensed real estate broker and spend a lot and most of my time on real estate rentals, subdivision development, et cetera. With this payout biweekly for the remainder of the year, can I qualify as REP (real estate professional) status for 2024?” – The prohibition to having W2 income is if you are actually working at your W2 job. Here, we’re not doing any work for that check. You’re just getting paid free money for 2024. You can go out and put your time into real estate.
  • “Given the time of the year that we’re getting into with taxes being due especially in the fall, what are the first three steps in the tax planning process, and how does one approach the process differently for clients that earn less?” – Start with having excellent bookkeeping, identify where you are today, and plan where you are going in the future.
  • “What is the best way to purchase an existing business for tax purposes?” – You’re going to buy the assets, you want to buy the assets because now you’re going to be able to get those at your fair market value that you pay for them. We call it stepped-up basis in your assets…
  • “If I buy a short-term rental and do a cost seg the next year, I bought it, and listed it on Airbnb, can I rent it long-term for the following year or would that interfere with the cost seg done the prior year?” –This is a common strategy, there’s nothing wrong with that – you want to at least rent it once in year one as a STR.
  • “If I claim bonus depreciation on my rental property, do I need to return or reverse it when I sell the property? What happens with bonus depreciation when I sell a rental property, or I necessarily have it in current?” – It depends on the transaction. If you sell a property then you have to have gain. If you don’t have gain on the sell, there is no depreciation recapture.


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Full Episode Transcript:

Toby:  All right. Welcome to Tax Tuesday. My name is Toby Mathis. Hey, Eliot, are you out there?

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