Hey team, I own two STRs that I actively manage. What is the best way to defensibly expense real estate mastermind fees? Are there important book keeping and entity structure considerations that affect the defensibility of the expense in the case of an audit? In my specific case, I’m looking at joining a mastermind that involves education, coaching, and hands on support analyzing real estate deals, operations, and networking opportunities. The mastermind is definitely real estate investing acquisitions and operations focussed, however it is not strictly related to the short term rental asset class. Is there any complication there with the mastermind involving expansion to a new asset class within real estate investing? My entity structure is such that each of the two MI based STRs is owned by a separate MI LLC. I also have a Wyoming holding company. ChatGPT recommended using the holding company to pay for broader real estate investing mastermind fees. A CPA friend recommended against doing that and recommended using one of the two MI LLCs that holds an STR expense the mastermind fee against. I want to make sure I’m doing it legitimately and as cleanly as possible. Thanks!

My wife and I are under contract on a property that we plan to use as an STR. I'd like to close into an LLC but it's not clear to me if I should put the LLC in only my name or if I should put both me and my wife's name on the LLC. We are a married couple filing jointly for taxes. Are there negative tax implications if I put both of our names on the LLC? Thank you!

If you’re planning to pick up a property in 2024, remember that you likely won’t qualify for the STR tax benefits on your 2025 return unless the property is placed in service during 2025. “Placed in service” means it’s ready and available for rent, not just purchased. It doesn’t need to have bookings yet, but it must be fully ready for guests. You’ll also need at least two paid guest stays to establish your average stay length and meet the 7-day rule. A few important reminders: - Stays cannot be to family at any price. Renting to family is treated as personal use by the IRS. - Stays also cannot be to friends unless you charge true fair market value. - You can use friends as paying guests if it’s an arm’s length transaction at full market rent. If you want a quick explainer on “placed in service,” here’s a helpful video: https://www.loom.com/share/69f59e1de5184d2782473dfbe7bd72c0 If you’re thinking about buying or want to make sure you’re on track for 2025, our team is here to help.