And he knows who's working regularly, who's only off-and-on, who's going through troubles, who needs extra work.

I don't know but I have plenty of Canadian and American friends and acquaintances who travel (regularly) to Mexico and the Dominican Republic but I don't actually know anybody who has vacation in Puerto Rico (unless they haven't told me of course).As can be expected, the most profitable form of real estate investment in the region is short-term rentals.

Quote from @Will Ghidotti: Hi Amby, I am a real estate attorney and handle this issue regularly.

Even updating the listing regularly so the OTA knows there's someone actually running the place behind the listing.

There's also regular inspections of both the living conditions and conditions of the home, and I've known some LLs in my area to fail for really stupid things (like a broken screen that the tenants must have broke), and if you fail no money until you pass. 

I just moved to Oklahoma City a couple weeks ago, but I will be coming back to Chico on a regular basis.

A senior product manager for Facebook Marketplace, where people buy and sell used goods, had regularly invested in startups run by friends or ex-colleagues.

They provide a lot of useful information for people but primarily focused on doctors regarding all types of investing including real estate, 401Ks and 403Bs, life insurance, disability insurance, regular investing accounts and more.

Make a list of places you would love to visit regularly and start digging into the market.  

The market rate for a full-service STR co-hosting company is 25% gross after cleaning fees.On average the following would be included... 24/7 guest communication, vender oversight, weekly updates on the OTA listings, make sure maintenance and deep cleanings get done...but owner pays the expense, stain removal on linens, marketing the property, keep supplies stocked...again owner pays the expense, keep property guidebooks updated (digital copy and hard copy), security (locks, cameras etc.) oversight, bi-weekly pricing software management, walk the property regularly, provide monthly reports, and obviously any guest problems that arise time to time.