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Tax Tuesdays
S-Corporation Tax Benefits: Why You Should Switch to an S-Corporation

Today’s Tax Tuesday episode answers several listener questions on S-Corps vs. LLCs. Eliot Thomas hosts with special guest Jeff Webb, CFO of Anderson Business Advisors. Online we have some of the staff from Anderson – Dana, Dutch, Ian, Piao, and Troy here answering live chat questions.

In this episode, you’ll hear our advice on several scenarios regarding potentially switching from an LLC to an S-Corp and the likely tax benefits, along with several questions about purchasing property for your children to live in while they are attending school or just getting on their feet. Submit your tax question to taxtuesday@andersonadvisors.


  • “I have an LLC now for a small business, and I’m wondering what the benefits are of switching to an S-Corp and what the tax deduction benefits might be?”— If it’s an LLC, it’s got liability protection. If it’s not making a lot of money, (under $50K) – probably don’t go the S-Corp route.
  • “Can cost segregation depreciation be done on a property purchased one or two years earlier? If so, is it state-specific? Would it be a great option if that was a possibility with REP status?” You can go back in time and do the cost segregation. Let’s say you bought the property in 2020. It’s now 2022. You could do cost segregation. That depreciation from the cost segregation would appear on your 2022 return. If you do not have REP status or can’t get REP status, normally cost segregation is not a great idea.
  • “Is there a way to convert from a 401(k) to an IUL (Indexed Universal Life) or Roth without having to pay the high tax burden, or at least minimize the tax hit?” The problem is you are going to get a tax hit if you take 401(k) money and put it in an IUL. Anything you take out the 401(k), money’s going to be taxed at ordinary rates. And if you’re not 59½, you could be hit with a 10% penalty on top of it.
  • “I’m a member of WREIN. I purchased a house and a condo in the past few months that two of my children currently live in. There is a mortgage and my soon-to-be daughter-in-law is on that with me. I pay the mortgage on the living costs, including tuition. Should I claim this home as a rental?” You can’t just write a check or gift it and say, now I’m going to have them pay me rent back. The IRS has seen through that. That’s a gift. It doesn’t sound like they’re paying anything so I see no rental here.
  • “My son is 26 and in his second year of post-secondary education. The condo doesn’t have a mortgage. I purchased it with funds from a private money lender in April that I have paid off with a HELOC from my primary residence. What would be the most advantageous way for me to claim this home, rent, and the best strategy? We’ve created a problem with our second home because we now have more than two private residences. Once again, I would probably deduct the HELOC as investment interest. Whichever one has the higher mortgage should be your second home. The next one would just be investment interest on an investment you own (the condo). And again, you can deduct the taxes on as many properties as you own. But again, you still have that $10,000 cap for state and local taxes.
  • “Due to having two W-2s, I cannot qualify for real estate professional status nor can my partner. What is the best solution to minimize the tax bill coming at the end of the year? By the way, with both W-2s, I will be moving to a higher tax bracket that neither W-2 knows about. I will owe more taxes than they take out at the end of the year, unless I find some way to get my passive losses from depreciation available to lower my W-2 bill.” If you make $50,000 in each job, you’re going to have a whole lot more taxes and probably going to be under-withheld because it’s based on $50,000 on each job. REP status doesn’t work. You could do a short-term rental. Be sure to adjust your W4s for two jobs/withholding.
  • “I just moved to Arkansas and sold and purchased properties here in Arkansas through a 1031. How do we get taxed on the remaining amount that was not used as a 1031 replacement property? I reserved some of the money from the sale as I don’t know what my tax bracket here is for taxation, and how much. I would be paying income tax. Can you give me an answer using the percentage of the sale?” Every dollar that you held back from the 1031 exchange is going to be taxed. And the first tax is going to be depreciation recapture, at a max of 25%. And the rest is capital gain at around 15%.
  • “I’m interested in using an accountable plan. Can you differentiate between a home office deduction,” which is on Schedule A, I believe, “and requires an exclusive home office use, versus the administrative home office which appears not to need the exclusive use?” ‘Unreimbursed employee expenses’ was eliminated at the end of 2017, so that doesn’t work anymore. Your only choice (especially in an S-Corporation) is a reimbursement.
  • “I’m not qualified as a REP (real estate professional) but with passive losses. Is there any way I can reduce my income with these losses and what can I do before this year is completed?” The only thing you can do with passive losses is offset them with a passive income, which effectively means you’re not using your passive losses to reduce your income. Short-term rentals are not rental activity.
  • “We have mainly W-2 income and also some investment properties passive. Our W-2 is too high to get tax deductions from its loss besides doing a short-term rental Airbnb. What are other ways we can deduct our W-2 income tax?” Max out those retirement contributions. Oil and gas is another still popular investment. There you have to have a working interest—that’s very important—but it is a write-off that’s substantially all of your investment for the most part.
  • “We are about to apply for a HELOC. We do not own our home yet. My husband is the only moneymaker right now. We want to buy my daughter a mobile home. It’s approximately $47,000. Our credit score is over 800.” I don’t think this is a business, and I think wrapping an LLC around this property is a bad idea. But the daughter would have to be paying market rent. You would have to run it as a real business.
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Full Episode Transcript:

Eliot: Hello everybody. My name is Eliot Thomas. This is our tax Tuesday for today. I’m sitting in for my boss, Toby Mathis, and I’m joined today by our CFO back from vacation, Jeff Webb.

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