http://www.connectinghaiti.com/
but the challenge is in how local governments regulate them. At the time that I was working there the very best internet money could buy as a consumer on our island was only about 4 MB which made certain types of things challenging. luckily I worked with a company that was in love with the idea of distributed teams, so they maintained virtual desktops in the United States that people could connect to do things where the slow bandwidth might mess with something important. Mainly things like executing code with our main data warehouse.
Another thing that you run into is access to a good consumer electronics market. If I am trying to get setup to work from home in the US it is easy to solve little problems, I can order things online and get them the next day or if I am impatient I can go directly to the store and buy usually exactly what I want to solve the problem. This won't be the case when you live on a small island, stores hit the general notes but if you are looking for something specific that you will know will solve a problem you may be disappointed. This can also be a risk if your primary machine goes down. I am not saying you should pack for the trip like a survivalist, but its important to think about things that could go wrong ahead of time so that you can plan for contingencies. Again my work being more than accommodating direct shipped me several items that I needed and pulled my ass out of the fire.
As to quality of life it can really be amazing. My company generally operated on Pacific time since all of the senior managers lived in California, as a result I would usually get up in the morning go to my surfing lessons lounge a bit then come home at around noon and start working.
As I sit typing this I am really starting to wonder why I ever came back to the US..... ::opens new tab to look at plane tickets::
However its great to have an little insight into what goes on in that corner of the globe!
What would probably bother me most are certain cultural differences. If they're majority conservative or religious they might go to extremes like hating or outlawing homosexuality, and most alternative culture would probably be frowned upon. Could be different now, but I remember hearing songs on the radio about killing all gay people...
Currently at a marina in Bonaire, close to Venezuela, connected to power/internet to do a remote contract. It's pretty sweet to go freediving or scuba diving a few feet away, then go to the "office" and work my ass off. Afterwards I'll be free again, sailing around for another bunch of months.
Challenges, well the obvious... getting distracted with the outdoors, oh man there is so much to do out there. But the pros are totally worth it and you strive to work hard to keep the lifestyle. If you really want it, everything will work out.
my search criteria was 35-42 feet, blue water capable, strong, proven old boat, $30k - $80k. It took me a few months of looking at boats online to get an idea of what I wanted. So many variables and unknowns and I hadn't even sailed seriously.
my training was a weekend sailing course in the NY harbour. After that, much reading... internet, books. There's a ton of info out there and you realize it's pretty doable.
after I finished working and could finally go and buy a boat, I knew exactly what I wanted. Bought the first boat I saw in person, after drooling for it for months and hoping nobody snatched it. She is a beauty and has treated me well these past few months jumping around the caribbean.
all in all it's a pretty good deal. For the price of a boat I get a home with the world as my backyard. I can't imagine living any other way at this point.