In this episode of Tax Tuesday, Toby Mathis brings tax knowledge to the masses and breaks down your tax questions LIVE! He’s joined by Jeff Webb, CPA and Tax Director at Anderson Business Advisors.

Updated April 20, 2021

Featured Questions

  • 00:10:43.01 – I received a large sum of money via inheritance in 2019. How can this amount be protected and have the tax burden minimized?
  • 00:14:03.05 – I am married and want to start my real estate business. My husband is not interested in any of these businesses. How should I proceed without interference from my husband for both tax purposes and asset protection?
  • 00:17:01.09 – I live in Illinois and I’m planning on starting a real estate business. I heard LLCs in Nevada, Wyoming, and Delaware are good. If I create an Illinois LLC, should I have any other of the three LLCs or should I just create a Wyoming LLC and not Illinois?
  • 00:22:11.01 – The current limit on home mortgage interest deductions is a max of $750,000 for loans after 2017. Does that mean that, if you have a loan for one million dollars, 75% of the interest is deductible or that none of it is?
  • 00:24:58.00 – I have paid $50,000 in legal retainer in a litigation case in 2017. The fees were withdrawn throughout the year 2018. There is still credit on the account as not the entire $50,000 was used yet. How can I deduct legal fees?
  • 00:27:04.05 – Is keeping a log of miles always required? How should the car be purchased so all the miles are considered business?
  • 00:33:14.07 – I sold an investment property in 2018 that I’d owned for more than 20 years. What is the tax liability on the sale of an investment property? What are the options for mitigating the tax liability?
  • 00:40:40.04 – I have an LLC taxed as C-Corp that manages my rental properties. It will not pay any wages and will operate at a loss for the next several years. It will provide fringe benefits. Can this entity sponsor a self-directed 401k plan to accept rollover contributions?
  • 00:43:32.06 – What is your opinion on cost segregation software, which can allow CPAs to prepare cost seg studies for $400? Is there any disadvantage for this versus physically sending someone to the property to do the cost seg?
  • 00:53:19.07 – If I make a large stock contribution to my 501(c)3, are there any capital allocation or income sourcing requirements that would force my charity to sell it off?
  • 00:55:51.01 – The loss from one pass-through rental LLC exceeds the gain of another. The LLCs are in different states. Do I pay state income tax with the profitable LLC even though I have federal losses?
  • 01:03:08.09 – If you buy a house as an investment property, hold it for five years, take depreciation for five years, sell it and do a 1031 exchange, what happens? Do you have to pay the depreciation back when you do the 1031 exchange?
  • 01:09:29.03 – I am initiating the sale of a California rental property that was held in my personal name. I will initiate a 1031 exchange, but would like to put it into an LLC for asset protection and tie into our management C-Corp to pay expenses.
  • 01:12:01.08 – Is a quitclaim deed sufficient to transfer the title of a timeshare from my personal name to a revocable living trust in California?
  • 01:15:20.05 – If you have a HELOC on your personal residence, which is in your personal name, and you use the HELOC to buy and renovate homes for your business, can you still deduct the HELOC interest as a business expense?