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.

I managed STR with my sister twenty years ago before Airbnb existed.

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.

. -- They have fixed fee structure to compare with anderson advisors without any blatant selling tactics https://www.kbkg.com/" class="redactor-autoparser-object">https://www.kbkg.com/https://go.empiretaxusa.com/61...If you attend any tax-wise or other 3 day events with anderson which costs $197 + travel expenses you will get enough knowledge on how they operate and you should be able to understand what LLC structure is beneficial, also they have a large collection of online videos with plentiful of information on youtube and tax tuesday webinars.

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

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