re: Ever thought of just giving it all up..

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on many islands outsider business owners arent very welcome and will be boycotted and pushed out of business.

Hell i knew a guy who wrote a successful tourist magazine for a few islands and the government deported him and he could not return. then they took over the magazine and "gave" it to one of the politically tied families on the islands

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This is true. I've been traveling and researching islands for several years now and an "American business owner friendly" island is a top priority.

ETA: The only way I'd live there full time is if I have a business. If not, the plan is to spend 3 months or so in the winter and then several subsequent visits of 10 days or so sprinkled throughout the year.

We are at the point now where we spend over a month every year in the islands so the next step is fairly logical for us. It doesn't work for everyone but it works for us.