To maximize return requires occasionally extracting value.  

In short, I'll never do it again unless the relationship began as a business relationship that later evolved into a friendship and even then I'd be very selective.In my experience, over time, lines got blurred and our relationship evolved to a point where every conversation mentioned the business in some capacity.

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. 

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

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.

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

Might suit me just fine for the occasional fax so I am going to look into it.FYI - https://app.hellofax.com/info/pricing

This is just the normal operating costs, never mind the big things that come up occasionally with capex like when you have to replace a major component (furnace, water heater, sewer line, driveway, steps, deck, windows, roof, doors, siding, landscaping, etc,) and it costs $10-20k.