Free Tax Tips & Strategies

In this episode of Tax Tuesday, tax attorney Toby Mathis, Esq. and CPA & Tax Director at Anderson Business Advisors, Jeff Webb, bring tax knowledge to the masses and answer your tax questions LIVE!

5:44 – If you experience a one-time large capital gain from exercising stock options, is it absolutely imperative that you figure out quarterly payments to avoid penalties, and if so, what if you missed April?

8:41 – An SMLLC that earned $20K in stocks – does it have to pay self-employment tax?

11:21 – How do I borrow against a stock versus selling the stock outright?

14:50 – To my knowledge, I can use a short-term rental up to 14 days or 10% of the total rented out days. I’m a REP. Can I take all the bonus depreciation in year 1 or must it be prorated based on my personal vs. business use?

23:55 – I bought a stock (USO) in 2020 and received a K-1. The stock price has more than doubled but I never sold any shares. Why do I have to pay tax for the gain which I never received? What happens when I sell that stock?

26:42 – Can we defer capital gains tax or spread across multiple years?

34:45 – Can I 1031 exchange from a single house rental into a percentage group rental? Or to a partial interest in multiple rentals?

39:08 – If I have a home in an LLC and have a property manager on the property, can I rent out the home to myself but have my employer pay my rent through the property management team?

45:41 – My accountant informed me that if I make over $150k annually, I would not be able to claim any deductions from STRs (short-term rentals). Can you explain this? Also, if I don’t provide “substantial service” for Airbnb, do I still need an LLC/C-Corp for management to decrease my taxes? I would like to report the income on Schedule E while writing off active STR income from 100 material participation hours.

51:26 – How does an LLC that’s a disregarded entity differ from a living trust in terms of estate planning? What if you have both? How do I use both in estate planning?

57:28 – Are the gains in a traditional SDIRA taxed the same as the rest of the money in the SDIRA when doing a conversion to a Roth SDIRA?

1:00:59 – If I buy a new house through a 1031 exchange, and I make it my personal residence after one year of renting it out, how long do I need to occupy it to qualify for the full Section 121 capital gains exclusion when I sell it?

1:09:52 – Can the 1244 rule be applied to an LLC that has not filed income tax in over 10 years?

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. One of my favorites as well is our Infinity Investing Workshop.

Additional Resources: