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.

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. 

Yet, as I closely monitor the current housing market, I realize that stability and thorough due diligence are paramount before taking ownership.

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.

One of the bedrooms on the ground level is currently my office, and I was considering keeping the desk, and buying a monitor & docking station.

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

The average temperature in the United States is 50 degrees, but if you are standing in Death Valley or Gnome, Alaska, what you experience may feel very different.In the handful of MSAs that I monitor, I'm seeing YoY rent changes from (2%) to 8%.