I did a quick Google search to see if I could find a good example of someone in the real world who has mastered the "island commute". Although the article is from 2000, I have found a good example:
Pat Stiley is a workers compensation and criminal-defense lawyer who has a practice based in Spokane, Wash., but lives in Belize. He uses the Internet to do legal research and also relies on cyber cafes and e-mail. Clients have met with him over the phone; Stiley still won his cases while arguing them in Superior Court via phone. "Except when interrupted by hurricanes, I'm usually online at least once a day," he says. "Not sure what my partners and employees think of all this, but I rather suspect they like having me out of their hair."
I did some further research to find out Mr. Stiley lives in San Pedro, Ambergis Key. Not bad.
I traveled to Belize in the mid-90s and absolutely loved it. Mr. Stiley, it appears, is definitely finding the lifestyle many of us only dream about.