[maryfield48]

A couple of insights from one of the poorer countries in the Caribbean, namely Jamaica.

Most currencies here are tied to the US$, so there has been no loss of purchasing power for US$ earners, other than in respect of goods imported from countries whose currency has strengthened against the US$. Short version, US$ will buy the same amount of locally produced goods, but will have lost purchasing power for European, Japanese, etc., goods. Just as it has if you are buying them in the USA.

Internet access - where there has been de-regulation of telecoms, there has been advances in access availability. DSL is readily available in the major towns/cities here. Elsewhere, dial-up is usually available, except perhaps in the smallest islands.

Don't count on the cost of living being a lot cheaper - there are many different nations in the Caribbean, with economies in varied states of health. Jamaica has a large debt burden that makes taxes & duties high, though it is highly likely that poker earnings would completely escape the authorities notice. Trinidad is an oil economy, and so is prospering now, many islands are dependent on bananas sold into an artificially price-maintained market through the EU, that is not likely to continue for very much longer.
Some things, especially involving labour, will be a lot cheaper, some things will be more expensive. You wouldn't like to know what a new car costs here - duties start at about 50% and go up to 180% depending on the engine size. On the other hand you can get some really great weed, really cheap.

The countries in the Caribbean do have immigration laws. You can't (legally) just come and hang out indefinitely. Having said that, many do. of course.