I used to live in Freeport. Just went there to visit friends. I have also considered trading from there but I think the phone system sucks (cable tv isn't very good either).
You can get a T1 (Internet), supposed to be on the backbone for $2K and there is always pirated satellite. How was it to live there?
Freeport is okay, not much to do on the island except drink and it is very hard to get a DWI. But the reef system is one of the best in the world. Great fishing and diving. For $2000 a month, you would probably try to share that right? The company I worked for (and this was about 10 years ago) had a shared T-1 but dropped it due to reliablity. Just getting a residential line was very difficult, usually you had to grab someone who was leaving the island and get theirs. If you decide to go there, let me know and I will put you in touch with my friend down there who runs a security firm (you'll need him).
The people there are very friendly, never been there, but from my experince in dealing with them have found them to be a very fun loving people. It also helps that I speak the language. I from Cuba, but Cuba is out of the question for NOW.