I probably should have pointed out in my earlier post that there were these other factors that influenced my decision not to own in that area again.

I created KBKG's Residential Cost Segregator software.

I have a LLC set up, and property management software ready to use.

For payments, tools like Stripe, PayPal, or booking software like OwnerRez work well.Happy to connect if you’d like to chat more or need additional tips!

In our student houses we use a programmable thermostat, but our building monitoring system has its own sensors and can override the wall thermostat and will not allow the temperature to get below 10C (50F) ... we are presently testing a new software load that will also prevent them from cooling the house too far in the summer.

The type of property can influence the risks you face, so coverage limits matter.

I suspect a decent VA could access public records and build a mainling list for you  or check Property Radar and see if there software will do that for you..

I think it may depend on whether or not their software catches the change.

Abandon the Peurto Rico dream for now and look at more realistic/beginner friendly areas that still sport a large latin influence and strong rentals, like Florida (I've looked a little bit outside Miami..Boca Raton, Tampa, West Palm Beach, etc). 

Does anyone have any tips or software tools to help give estimates on pricing and the potential occupancy of the rental?