Even large and small businesses with intangible residual services like TV, internet, security, pest control or the local contractor with remodels in process could fall behind on payments revenue contract. 

Rent payments from the medical LLC are fully deductible as a business expense, while the property-owning LLC will report the rent as taxable income, which can be offset by deductions for expenses like mortgage interest, property taxes, maintenance, and depreciation.To ensure compliance, document how FMV was determined—using market comparisons, an appraisal, or similar data—and draft a formal lease agreement outlining the terms, rent amount, and responsibilities.

These properties cover my mortgage, allow me to save for maintenance/repairs, and are projected to be worth $7–9 million by retirement.

You’ll need to treat it like a business—handling tenant management, accounting, legal compliance, property maintenance, and more.That said, when done correctly, it’s a powerful tool for building wealth!

Because real estate always goes up and the maintenance fairy takes care of all repairs free of charge.Seems like a recipe for disaster. 

Also, the turnover will be much lower, but maintenance costs might shift too, so it's good to plan for that.Happy to connect if you need more tips!

Since it's mortgage-free, the rental income would be mostly profit (after expenses such as property taxes, insurance, maintenance, etc.).

I just bought a $400k STR and the break even point with 25% down is $54k with a 2% sinking fund and 3% maintenance built in. 

Here's a list of things to track:- Formal lease application- Formal signed and executed lease specific to your state- Payment history (I recommend using online rent collection like Apartments.com, RentRedi, etc)- Maintenance requests and receipts- Accounting for all rental-related expenses (repairs, utilities, etc) The more you treat it like a business, the more helpful you are to your CPA come tax time. 

I'd check local STR FB groups and see if you have a local Real Estate Club.You can offer your services there, maybe for free in exchange for the experience.