@Ryan Duphorn  a  5 /2  and 1920 square feet IMHO isn't a good health care traveler accommodation unless you are in a area with a shortage of housing. 

We used to travel up there 3-4 times a year. 

Our STR/MTR portfolio typically sees around 80% occupancy, and I’ve noticed that the online travel booking sites often push properties with consistently great guest experiences.

Due to our love of traveling and hating the negatives that LTR brings along, we prefer STR and offering the same memorable experiences to travelers that we have experienced when traveling.

Looking for various tax strategies to reduce the reality that a large RV or boat is a grossly depreciating assetI would not have a loan, so claiming it as a primary or secondary residence and claiming the mortgage deduction is not applicable.I sold my primary residence and I have several rental properties which I use as I'm fixing them up.What I'm pondering is living aboard and working aboard developing a new product, while traveling.  

I have a solution that I do myself once a year.Here's one of my best tips: go on Airbnb as a TRAVELER, in Traveler mode.

We cater to families and groups traveling for the lake and the bike trails so we designed based on those demographics.

I'm from Louisville KY and traveled to Bloomington for a Big Box company as a trainer.

Rodrigues' recommendation may change this), but my next question would be, are there any cities/markets where 1 of the following are true: 1) You have family/friends that live there, 2) You travel there frequently (either for vacation, work, etc.), or 3) Somewhere else you've lived before AND know the area well?

I'm an investor (STR properties), realtor, and own a construction company near Texas A&M in the Bryan / CS area but travel to the 903 frequently to visit family.