In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., answer listener questions on tax planning, entity structuring, and asset protection for real estate investors. They discuss the best tax strategies for investors who own multiple rental properties as sole proprietors and examine whether converting an S Corporation that owns rental property into an LLC could trigger property tax reassessments or other tax consequences. Amanda and Eliot also explain the rules surrounding home office deductions, including using a detached ADU as a dedicated workspace and claiming deductions for business storage in a garage. They cover the differences between operating as an S Corporation with an accountable plan versus filing on Schedule C, addressing common concerns about IRS scrutiny. Finally, they explore the complexities of structuring a 1031 exchange alongside a self-directed Solo 401(k), highlighting prohibited transaction rules, financing considerations, and strategies for staying compliant while maximizing tax benefits. Tune in for practical guidance on protecting your investments and making informed tax decisions.
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Highlights/Topics:
0:00 Intro
9:29 I work in a family-owned company and have the opportunity at the end of this year to obtain equity/ownership. Would you recommend accepting that ownership under a specific tax strategy or corporate setup, or just accepting the ownership under my name and Social Security number?
18:26 Is it a good idea to pull money from a traditional IRA early and then invest in oil funds to get IDC deductions to help offset the taxes I will incur by withdrawing from the IRA?
23:25 Can tax documents be reviewed for previous years and if my previous preparer didn’t use all the available strategies; can those strategies be applied for those years?
27:32 I will be relocating to South Africa which has a tax treaty with the United States Government. I am a retiree who receives a monthly annuity. Will I be double taxed? I will be paying both federal and state taxes in the USA.
34:36 What is the best tax strategy for sole proprietor ownership of 12 rentals?
40:50 I have a 22-unit condo project that we converted into rentals in 1992. It was a C Corp. Now it is an S corp. One adviser suggested converting to an LLC. Would this trigger a taxable event for property tax assessments?
47:23 I have a detached ADU in my backyard. I want to use it as a home office. Can I do that and if so, how is the deduction calculated? Also, can I get a deduction if I use part of my garage for the business for storage?
53:59 Does a Sub-S election with an accountable plan attract more attention than a Schedule C filer?
57:07 We are completing a 1031 exchange and would like guidance on the best way to structure the purchase of our replacement property. Our objective is to use all available 1031 exchange proceeds while funding the remaining balance with assets from a self-directed Solo 401(k), if permissible, and avoid obtaining a conventional mortgage. Are there any IRS rules, prohibited transaction concerns, or tax implications we should be aware of before proceeding?
