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Tax Tuesdays
How To Report Income From A Short-Term Rental Property

Today, experts Toby Mathis, Esq., and Elliot Thomas, Esq., explain valuable tax strategies for real estate investors, traders, and various income earners. You’ll hear about the optimal tax classifications for short-term rentals, using retirement funds for real estate investment, and the transition from W-2 to 1099 income for tax benefits. Additionally, Eliot and Toby discuss maximizing deductions through trading partnerships, the benefits of Health Savings Accounts, vehicle write-offs, and home office deductions. Submit your tax question to taxtuesday@andersonadvisors.


  • Is short -term Airbnb and VRBO (short term rentals) under Schedule C or Schedule E? – if it’s just bare oversight management, etc. That might put it on Schedule E. Schedule C is if you have more substantive activity you’re putting into it.
  • I was told I could use my company assets of 401k to loan money to buy real estate investment. Is that true? If so, how? – its true, one is allowed to take a loan out by law, if your plan allows for it. If you don’t pay it back it becomes taxable income.
  • How how can I position my child’s college tuition as a business expense? – let’s say your child’s handling the bookkeeping for your corporation, and they’re taking accounting classes, then you can deduct the classes related to what that child’s already doing in the corporation.
  • What percentage of gains do I need to pay tax on if I trade for it, if I trade forex and if I put money into a holding LLC? Can I minimize it? – often it’s gonna be section 1256, and You get a treat 60% as a long-term capital gain, and the other 40% is gonna be short-term capital gains, which means you’re at your ordinary tax bracket rates.
  • How do I deduct expenses if I have a W2 and a 1099? – generally speaking, on a W-2, there’s nothing you can deduct business-wise against. If you had expenses that you incurred in order to get your W-2 income, they took that section away with the Tax Cut and Jobs Act back in 17.
  • I just started my small business of being a mortgage broker. I own a single family rental about an hour from my house. Can I take a tax deduction for mileage expenses if I use my vehicle for both businesses? What about taking deduction on one car for mortgage and take deductions on the other car for the rental property? – We’re going to recommend your vehicles be titled in your personal name. Usually we’re going to deduct that mileage.
  • If I purchased a property to rent it and I have it as an Airbnb and I did a lot of work in 2023, can I claim all the expenses for 2023 tax year, even if the house was not rented at all in 2023 because of work is estimated to be complete in quarter one of 2024. – You can in 2024, but we can’t go back to ‘23, when the expenses were incurred, because it wasn’t placed in service yet.
  • Can I make charitable contributions from my business LLC income and take it as a business tax deduction? Due to the standard deduction, I can’t deduct them from my personal return. – If it’s a C corporation, then the C corporation can deduct up to 10% of its net income. Used to be 25% during the CARES Act but they’ve moved it back to the traditional 10% of your net income
  • Started regular 15-year depreciation for capital improvement of rental property in 2021, didn’t know any better. I switched to bonus depreciation and claimed the remaining amount in 2023. Are any home improvement projects tax deductible? – At its base level, no. But if you happen to have a home office, and you have a C corporation or an S corporation, then any your home improvement projects, yes, they will be deductible in the sense that if it’s directly related to the office


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Full Episode Transcript:

Toby: Welcome to Tax Tuesday. My name is Toby Mathis.

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