Quote from @Gregory Wilson: A few things there, Brendan.First, an LLC with you as a member and your (wife, son, pal, etc.) partner as a 1% member will file a Form 1065 which is about one tenth as likely to be audited by the IRS as a Form 1040 with a Schedule E rental activity (which I presume you will attempt to show is an active business).Second, you want an LLC because when your local Alabama handyman drives his girlfriend's uninsured truck into a van load of U of A medical school interns on I-22 when he goes  to get some shingles for your roof, on your business, you don't lose everything you have or ever will have to an uninsured claim. 

Although most of my stays are <7 days, I've had a few longer stays (business travelers and a family that was going through a full home remodel).

I was wondering how people managed to scale their businesses faster.

I’ve been in the real estate business as a broker, helping clients buy and sell homes, but I’m looking to take things to the next level by diving deeper into investing.

- sounds like your friend's PMC pays this way.If W-2, why isn't your business properly insured to cover him?.

That's smart business, right?

From real estate investors to other small businesses, I talk to people daily who have no idea about the potential liability under the Telephone Consumer Protection Act ("TCPA")(47 U.S.C. 227 et seq.).There are two initial issues that can create huge problems with your suggestion.

We're living in times when franchises go out of business overnight, but healthcare will never be since it is essential. 

There may be a way to reduce property tax reassessment by using LLCs, but it is a complicated plan, takes time to complete, generally needs a business purpose, and is not without risk. 

I took the course last October... got swamped in my currently real estate business... went through a 90 day "challenge" course with RAL academy....