We're bootstapping here and I'd say its paradise. Beaches in the morning to work and then by evening we duck into our local for a pint and some more work.
Even with ridiculously long days its relaxing.
Rent = ~$350/month (clean bungalow, 5 - 10 min walk to the beach with internet)
Good Internet = ~$40/month or so If you get setup with a SIM card and TrueMove, they have WiFi around the island that does a respectable 8mbit and ~1mbit up
Food = ~$3 - 10 per meal depending on how much food you get. You can go cheaper, but thats for convenience (prices of restaurants in the area we work)
Drinks = ~$0.50 - 4 this depends where you go, but a mojito in our regular is around $2.50
Feel free to get in touch if you plan on coming out! jamil@player.me