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?