Occasionally see places in Weatherford, Azle, and Bridgeport. 

I now have the card where I can use it occasionally and it will add to the amount of available credit.

To maximize return requires occasionally extracting value.  

If 2x, 3x, 10x the # of burger trucks flood onto a given street to offer burgers to the people, to meet demand 1:1 it has an economic effect of competion driving prices to REMOVE any bloat, any false margins, right.

We would use it 1 week a year (like we do now) so the 3K we'd normally pay would be used by the condo and the occasional get away during off-season.

Distance makes investing more challenging, as does seasonal occupancy and governments which operate differently and/or are less stable than our own(though our own government has not been a paragon of stability lately.)By investing in the Caribbean, you’re adding those challenges plus you’re throwing in the occasional hurricane.  

Yes, you should ask about wind insurance as we do get wind damage occasionally from hurricanes although it is far milder than the coastal areas. 

Occasionally, I still experience "impostor syndrome" and feel like I can't do what I'm doing even though there is plenty of evidence to the contrary.

I have a fax machine / scanner/ copier and occasionally fax.

That's very common here, with the occasional $250 or $500 offered instead.