In this episode of Tax Tuesday, Toby Mathis, Esq. brings tax knowledge to the masses and answers your tax questions LIVE! He’s joined by Toni Covey, enrolled agent (EA) and Director of Professional Services at Anderson Business Advisors.


Updated October 20, 2020

Featured Questions

  • 11:57 – I have an empty plot of land. If I sell it and have a loss, am I able to write off the loss on my taxes?
  • 18:55 – Can one set up a hedge fund for an entity so that you can trade stocks and not be taxed as long as the proceeds stay in the fund until they are reinvested?
  • 25:10 – Are there any strategies to reduce paying taxes on benefit or pension income and Social Security benefits? If so, what are they?
  • 35:06 – Can I use my self-directed IRA as a hard money lender?
  • 45:20 – I have noticed that taxes on new construction properties are generally lower for a year or two before increasing. Why?
  • 54:39 – How can I avoid the transfer tax in FL when buying residential rental property with a loan and transferring to an LLC? Also, how much do land trusts cost?
  • 58:33 – Can I take a $100k distribution from my 457 account and contribute it to my housing nonprofit under the 2020 CARES Act’s 100% AGI charity contributor?
  • 1:04:54 – Does receipt of a disaster loan and PPP affect taxes?
  • 1:11:32 – If I have two rental properties, should I go for two LLCs or only one?
  • 1:12:56 – Can I use a self-directed IRA to fund the purchase of distressed mortgage notes using a C-corp?
  • 1:19:35 – If you’re a full-time stock trader, do you qualify for unemployment if you go bust?
  • 1:22:15 – I have several rental properties (but no legal entity) and reported a loss on my 2019 taxes. Do I qualify to apply for an EIDL?
  • 1:23:31 – How do 1031 exchanges work if properties are held in an LLC?
  • 1:27:07 – If I do a 1031 exchange from a CA property to a NV property, what taxes will I owe?
  • 1:31:33 – Under the CARES Act, I borrowed $100,000 from my 401(k). Does the remaining balance remain invested as before? What about the repayments I make?

As always, take advantage of our free educational content and every other Tuesday we have Toby’s Tax Tuesday, a great educational series. Our Structure Implementation Series answers your questions about how to structure your business entities to protect you and your assets.

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