My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

So Keep your property but don't mid-term unless it is very small house and would appeal to traveling nurses on 3 month gigs.

Quote from @Mike Grudzien: Two thoughts:1) stay in your STR for a day or two and you'll discover things it needs or that would be nice to add2) use several touch-points to communicate with Travelers/Guests.

I suppose I could combine the two ideas and live in a basement while renting out a 2 bedroom home to a traveling agency. 

There are many more and many more personal goals such as getting married and starting a family, adopting my first GSP dog, traveling to Wyoming and Montana and spending more time in nature, just to share a few.

Temporary work travelers etc.

Add thoughtful touches like a Keurig or French press, USB chargers, and local travel guides.

Positive SolutionsProblem: In my county small multi-family houses are nearly non-existent and short-term rentals and second-cooking-areas are illegal.Solution: House-hack while renting MTR to traveling medical professionalsProblem: I didn’t know the many laws of the countySolution: A hired attorney 1) informed me that the county calls a house-hack a boardinghouse and 2) drafted a very comprehensive agreement that includes answers to your list of questions.Problem: Interpersonal problems can be a risk.

Lots of medical in KC - hospitals, medical school, etc.

@Jon Latorre I'm traveling to CR next week.