Welcome to the forum. Lots already here to read as well as sections to direct your questions.
1. The chain of Islands beginning in FL clockwise around is about 2,000+ nm to Central America
. There are of course any number of places along the way. I suppose depending on what takes your interest a lifetime is maybe enough for an overview.
2. I'm not sure what you might mean by downsides. It's not like what you are used to so maybe that is an upside. There are differences in many places as far as about anything you can think of. Climate and culture vary quite a bit. Some places are very expensive.
3. For hurricanes you have a few options. The first, leave during hurricane
season. second, haul the boat out of the water
and secure it, or go uninsured and risk it all including the liability for anything the boat destroys and the mess it makes. This generally becomes a process of dealing with how your insurance
works. Costs will vary greatly depending on where you are.
4. The beginner may be faced with some challenges depending on location and time of year. When the trade
winds kick in and the winds blow strong and steady with the bright blue sky it is quite enjoyable but these are not "gentle" breezes. You can island hop so that means you can pick your weather
to match the conditions you can handle. That is what most people do.
I would say cruising is not easy for a beginner any place. Lots to learn about the boat, skills, and the equipment
. Then throw in the places, the laws, the languages, and all the things you are not used to and it requires a change in yourself. Some people can adapt and others can not change. The idea of it is not the same as doing it.