For those wanting to buy a property in the Caribbean and move down full time, there are options. For most, the easiest way of doing this would be through a Residency Permit. These permits allow you to live in the country for a set number of years (renewable), without much difficulty. The fees are minimal and the qualification is easy.
One thing your residency permit will not allow you to do is work while living in the country. These permits only allow you to live off of monies sourced in your home country (ie retirement or business income). This is why these permits are so east to get versus a work permit which is a much more difficult to qualify for and quite a bit more expensive.
A Work Permit requires an employer to prove that no local is able to do the job. This can be a high bar depending on the position and the employment situation on the island at the time. Work permits are for a predetermined length of time and are by no means the rubber stamp that you can expect with a residency permit.
Yes, there can be other differences as well. One of the bigger issues can be national health insurance, which is usually reserved for those with a work permit, although these issues are being reviewed all the time.
For most people looking to move to the Caribbean full time with no need to work, a residency permit is more than enough. Another option in some countries could be the citizenship with investment programs. This program is obviously better than simple residency however not all Caribbean countries are on board with these programs yet.
Here are just a few of the countries offering the citizenship programs.