., San Diego, and others)—making it feel like a “natural” choice for a regional traveller wanting to get away for a short weekend. 

Managing five rentals can eat up a ton of time in any given week, often at times that are inconvenient to you and your personal interests (family, hobbies, travel, etc.).Of course you can manage on your own.

@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. 

Not only do we find the housing market to be a little more manageable, but a lot of people travel there year round. 

The profile of the typical Houston traveler is someone coming in for work.

I live in Honolulu currently but used to live in Tokyo (mother is Japanese) and still travel there on a regular basis (pre-Covid).

California's probate rules can be drastic in the event of death that having a proper estate plan in place can help in any number of situations, including if just traveling or incapacitated.These are all things you will want to discuss with your attorney and CPA.

Being in the Army limits my ability to travel and explore markets firsthand.

We exclusively travel during non-peak seasons, so we would be looking to rent out completely during busy/peak seasons, and would stay at the place during slow seasonsQuestions for the experts out there:1. which development(s) tends to be the best for ROI/have the best occupancy rates?

My new primary residence in Oregon will not be in an LLC however I intend to travel off and on, and rent it out but that won't occur for another year or so.