Exploring Tax Strategies and Medical Reimbursements

In this Tax Tuesday episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., explore the limitations of renting home office space to yourself as a sole proprietor and explain superior alternatives through S and C corporations that unlock better deductions and reimbursement opportunities. The attorneys provide detailed guidance on properly paying children through family businesses to maximize tax benefits while avoiding employment taxes, and discuss the complexities of transferring real estate to children through gift strategies. They dive deep into syndication investments, explaining passive income treatment, cost segregation benefits, and how real estate professional status can transform passive losses into active deductions. Other key topics include the master lease strategy for short-term rental owners seeking to optimize tax benefits, the mechanics and restrictions of 1031 exchanges, medical expense reimbursements through C corporations (including controversial deductions for specialty foods and safety equipment), and the proper setup timeline for nonprofit organizations. Tune in for expert insights on these advanced tax strategies and more!

Submit your tax question to taxtuesday@andersonadvisors.com

• "Can I rent my home office to myself as a sole proprietor?" - No, use home office deduction instead.
• "I know an owner of a small business can pay their kids to work for their company. I've heard several different facts about how exactly to do that, which contradict one another. Can you please explain the proper steps?" - Pay kids W-2 from sole prop, avoid taxes.
• "We were advised to transfer real estate to our children up to a certain limit using the parent-child transfer provision form 709. Can you please discuss the advantages and disadvantages? Any limitations on the amount of equity transfer and any IRS requirements, etc.?" - Not recommended, complex bookkeeping, lose stepped-up basis.
• "I want to join a syndication as a limited partner. What tax implications do I face at the time of distribution of profits and how does it change if they do a cost segregation and bonus depreciation while I'm still part of this syndication? An additional fact is that this person has their own long-term rental." - Passive income, and cost segregation create offsetting losses.
• "Are you entitled to cost segregation benefits if you invest in a syndication with your IRA/401k funds?" - Yes allocated, but no tax benefit in retirement.
• "Please explain the C Corporation Master Lease strategy for short-term rental owners. I own a short-term rental but was unable to capitalize on the short-term rental loophole because I had used professional property management. Does this strategy provide any advantage to somebody in my situation or allow me to take advantage of the loophole in a different way? How would the tax breakdown work in this case if I created a management C corporation?" - C corp manages property, shifts income, enables reimbursements.
• "What is the downside of using a 1031 exchange to avoid taxes in a profit transaction? Are there any benefits?" - Strict deadlines, higher debt required, but defers taxes.
• "What are the medical expenses aside from doctor visits and out-of-pocket medications allowed as reimbursable from the C corp? A doctor has recommended including antioxidant foods in our diet to improve my spouse's diet due to a specific condition. Is it reimbursable if we buy foods that are not really on our regular grocery list? Only because our doctor suggested it. Additionally, the other day, my spouse slipped on one of the floor mats, so I had to buy rug grippers. Is this also reimbursable?" - Doctor's note rule applies, antioxidants questionable, grippers no.
• "I would like to know if I can start a business as a nonprofit before I begin doing the work. Or do I have to already be up and running?" - Set up a nonprofit entity first for protection.

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