Working remotely for the month of February – where to go in the Caribbean?

We’re in our mid 50’s and looking to escape the snowy Midwest for roughly the month of February. I would appreciate some help narrowing down the possibilities. Our priorities are:

1) Reliable internet and power, since I’ll be working remotely part-time

2) Safety, including personal safety and decent medical services available in English if needed

3) A decent airbnb or similar, 2 bedrooms for $100/night or so, close to a town, beach, and hiking

4) Decent weather for swimming (warm and calm water)

5) Nothing too close to Venezuela since who knows what Trump will do next

6) Direct flight from ORD would be a bonus

Thanks!