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Tax Tuesdays
LLC vs S-Corp: Which One Is More Beneficial For Your Business?

Welcome to another Tax Tuesday show. Toby Mathis, Esq., hosts, with special guest Eliot Thomas from Anderson Advisors, and they are here to help answer your questions. On today’s episode, Eliot and Toby dig into some listener questions surrounding the differences between an LLC and S-Corp and the pros and cons of each, avoiding capital gains taxes, and the usual assortment of questions about short-term rental properties (ie AirBnB), cost segregation, and qualifications to claim Real Estate Professional status.

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


  • “If I choose cost segregation, do I have to apply the cost seg to all properties purchased in the same year, previous years, and future years? What are the disadvantages—tax aspects and non-tax aspects—of doing a cost segregation?” – If you do a cost seg, you’re not required to use it on your other properties. That’s very specific to one property.
  • “I bought an apartment to fix it and put it up in Airbnb and to get the advantage of new business tax deductions. But now that we are thinking of renting it to regular tenants, this will be an investment instead of a business, correct? What are some of the deductions that we can take advantage of if we rent it to regular tenants instead of Airbnb such as renovations, expenses, travel expenses, furniture, and so on and so forth?” – Turning it into a long-term rental, you pretty much get some of the same deductions you would as a long-term versus short-term. They’re the same.
  • “Is it beneficial to set up an LLC versus an S-corp? And are you able to pay yourself a reasonable salary through an LLC?”- There are rules behind that. If you don’t choose a tax status forth, the IRS will choose for you the basics… like Eliot said, it depends on how the LLC is taxed.
  • “How should I hold my stock positions? What is the best way to deal with high capital gains consequences?” – We often talk about setting up a trading partnership, that might be one option.
  • “My husband will work as a real estate agent to qualify for the IRS’ definition of real estate professional, and potentially use the passive losses from our rental property to offset my W-2 income on our joint return. The IRS rule says my husband has to own at least 5% interest in the real estate company employing him. Does he need to form an S-corp to sign the contract with the brokerage firm so that he owns at least 5% interest?” – Yes, that’s exactly right. You’re going to want to have his earnings, if you will, from there being paid through an S-corporation that he owns, theoretically 100%, hopefully.
  • “I sold an investment property on October 21 and paid a very heavy capital gains tax. Can I get some of that back if I buy another investment property today or now?” – No. We missed the boat on that. We can’t carry back on any of these items at this point in the code. Maybe that’ll change in the future, but right now, we don’t have the ability to go back and change anything.
  • “How many years can we go back without showing a profit?” – If you have too much of a loss, the IRS could come in and say, hey, is this really a for-profit business venture that you have going on here?
  • “Is it okay to do your own taxes as a business owner if you had a CPA for 20 years?” Why is it a questionable call there? – We just had a massive overhaul of our tax code. You’re going to want a CPA, somebody who does taxes, EA, tax attorney, whoever it is, to walk you through some of those things.
  • “I bought a single family rental in November and am still repairing. No income yet. How do I record depreciation and costs for 2022?” – If we didn’t have it available for rent in 2022, there isn’t any deduction to take in those as far as operational, depreciation, or anything like that.
  • “How to save taxes by flipping and renting houses?” – We’re going to recommend a C -Corp probably as a management company so you can do all your activities that you’re overseeing of your rentals through a C-corporation.
  • “I just started my business in August of 2022. I would like to understand what from a tax perspective should be on the top of my mind as we prepare the first returns.” – It depends on your business, but you’re going to want to categorize and have an idea of what expenses are, to determine whether it’s a net profit or net loss.
  • Lastly, “If an investor purchases a property that is lower in value than the property sold in a 1031 exchange, will the IRS disqualify the exchange entirely?” – No. What’s going to happen is you just may not have full deferment of the capital gains, but they’re not going to disqualify it on that premise. Work with a qualified intermediary!
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Full Episode Transcript:

Toby: All right, guys. Welcome to Tax Tuesday. My name is Toby Mathis. Eliot, you’re way out there in Vegas right now, right?

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