In this special Maui-edition of Tax Tuesday, Toby Mathis brings tax knowledge to the masses and breaks down your tax questions LIVE from Anderson’s 2019 Executive Retreat for Real Estate Investors! He’s joined by special guest Michael Bowman and other Executive Retreat attendees and speakers.

Updated March 16, 2021

Featured questions:

• I have several LLCs taxed as partnerships. I buy foreclosures. Recently, I acquired a property and decided to sell, without improvements, for about the price I foreclosed (10% gain). Can I still maintain my passive status in that LLC for this year even though I “flipped/resold” this one property in 6 months?
• I am closing on the sale of a property purchased with my LLC of my solo 401(k). Is there a tax benefit of paying a JV partner from the LLC’s bank account versus directly from escrow? Meaning, does paying out of escrow reduce the profit that would be subject to tax?
• Can I take advantage of business deductions (for travel, education, conferences) if I do not directly own rental properties and instead invest in real estate as a limited partner in syndications and funds that generate K-1s?
• I have created a management C-corp that manages all my different LLCs and properties. I am not taking any salary out of this corporation at this time. This C-corp has an employee welfare plan that pays for my out-of-pocket medical expenses. My question is: from this plan, can I reimburse myself for my employee contributions to my W-2 job’s healthcare plan?
• If I purchase a property within an Opportunity Zone and start a business based from that building, which passes the Opportunity Zone tests, do I still need to improve the property, as well?
• I plan on having my Wyoming LLC become the 100% shareholder of my two C-corps (one C-corp for flipping homes and one for flipping raw land). Will my LLC have to file a tax return even if I zero out the revenue with expenses and a salary for myself?
• If a person uses cost segregation on a rental home, isn’t the depreciation recaptured upon the sale of the home? Can a 1031 exchange be used?
• What’s the best entity structure for Airbnb, HomeAway, and VRBO? My plan is to sign long-term leases (12 months) and rent on these platforms.

Watch now as Toby Mathis, Michael Bowman, and other special guests from Maui break down complicated tax laws to make them easier to understand, helping you save your hard-earned money.

Click here to register for the next Tax Tuesday & submit your tax questions for answers from the pros!