You should never use a debit card or pay for medical expenses from your HSA, ever!

On paper, a restaurant manager with a 740, may appear stable, but is it more stable than say a medical tech in healthcare with a 640, with less or equal time on their jobs?

Similarly, if you are you a medical professional with strong connections at the local hospital, then target properties (and their owners) that would attract medical travelers.

Quote from @Neil Quinlan: Thank you and yes I am vested with my department thankfully and have 15 years until medical is paid.

I want to make sure I'm not missing something.I can withdraw penalty free from prior Roth contributions and 5+ year old conversions, an inherited tradtional IRA, an HSA with prior medical receipts, among several other options.

Long-term rentals are a solid choice, but mid-term rentals in medical hubs (like yours) can offer strong cash flow with less turnover. 

There's supposedly a large medical center being planned, which will also need convenient housing.

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. 

I am a resident physician in dermatology, during  medical school I bought a property in Denver with an Interest rate of 2.75% (COVID rates lol) with the goals of renting it out when I moved onto the residency.

good medical at emergency!