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Tax Tuesdays
Tax Tuesday with Toby Mathis 10-16-18

Toby Mathis and Jeff Webb of Anderson Advisors like to talk about taxes. It’s a lot of fun for them, and hopefully, it’s educational for you. Do you have a tax question? Submit it to taxtuesday@andersonadvisors


  • We have a vacation rental that we’re rehabbing. Should we form an LLC to collect rents? Don’t put your rental in your corporation; if you take it out, it’s considered wages
  • If the rental is an LLC and you want to flow it to the corp, isn’t that contribution LLC to corp? No. If you want the money to go to the corp, you’re paying in a management fee
  • I’ve taken real estate training and investing using my LLC’s credit card. Can I deduct those courses? If it’s a new business, no; if it’s an existing business, yes
  • Travel Meals: If included in lodging, is it 50% or 100%? Depends on how you’re billed for travel; if items aren’t separated out on a bill, they’re 100% deductible
  • How much can someone loan or gift to you in a single year and it not be a taxable event? $15,000 a year per recipient; if it’s more than that, you have to file a gift tax return
  • I’m a self-employed life insurance agent and want to wholesale properties. How should I structure both businesses? Licensed agent is an S Corp; wholesaling is an S or C Corp
  • How does the process change, if the rental LLC is owned by a Qualified Retirement Plan? It can’t be a second/vacation house because you’re a disqualified party as a QRP
  • Is this LLC with rental and income qualify for the 20% pass through? If real estate is triple-net lease, it doesn’t qualify for 199A; if not triple-net, you get the 20%
  • My condo’s roof has a bad leak, and it took 8 months to fix it, during which it couldn’t be rented. Can I declare it as a rental for the entire year? Yes
  • If I buy a house subject to rent it out, does the income on the property go toward my person or business? The personal owner, unless you put it in the LLC
  • I manage 10+ single-family houses. Can I deduct 100% of cell phone and Internet expenses? If through a corporation, then yes; if sole proprietor, write off business portion
  • What if you loan money to your LLC, is there imputed interest? You can’t impute interest to yourself; but if it’s a separate taxpayer, then you have imputed interest
  • What if I rent a hotel or Airbnb when I’m looking for an investment property? Set up a corporation to write off those types of expenses
  • Can you deduct food expense when going to a cafe to do office work on your laptop? If it’s your business, yes; if going there to do office work on your laptop, it’s not deductible
  • Our mom’s condo was put into three siblings names. We sold it. Should we put it in a trust? You should have kept it the mom’s name to pass it on with a step-up-in basis
  • We would like to own a house in Florida, but keep our house in Georgia. Tax wise, which is better for a home-based business? No income tax with a home jurisdiction of Florida, and you don’t have any ALS tax

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Section 179 Recapture

Section 179

1244 Stock Collection


Woody v. Comm, T.C. Memo. 2009-93

Section 195



1031 Exchange

Affordable Care Act


Schedule A

121 Exclusion



Tax Wise Live Stream

Anderson Advisors Tax and Asset Protection Event

Toby Mathis

Anderson Advisors

Full Episode Transcript:

Toby: Hey good evening everybody or afternoon depending on where you’re at this is Toby Mathis and Jeff Webb.

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