Quasi-retirement in CI: is it possible if you're not wealthy?

You didn't say whether you have read my Forum post nine lines below yours. I presume you have, though you didn't mention it. Also the post two lines below that, called "Doing business..." It would be useful for you to go through the relevant posts on my personal blog, too; just skip over the ones that don't seem relevant. (You have to click on my name and then hit the "my blog" button on the menu.) Once you've done all that, you will have some specific questions; I'll be glad to answer them.

Thanks Gordon! I actually found your post after I submitted my question, and did go on to read some your personal blog entries (excellent and extremely well-written!).

There are some older posts on your blog that I still need to read, but it seems as though my general impression is correct and that the only real option would be for us to apply for an extension of our visitor permit every 6m. (Do you agree with that conclusion?) Do you have any insight into the success rate for such extensions, and/or what the CI Immigration Board considers "sufficient income," which is not defined on the Visitor Permit Extension application form I found online?

Much depends on how flexible you are. As a tourist/visitor, you would have no income requirement, but of course no right to reside; you might have to leave the Islands every few months. (No big deal; you could go to Miami and do some shopping, to stave off "rock fever"!) As consultants, as long as your clients are offshore and stay there, you don't need a Trade & Business Licence. For LOCAL work, you might not get a Licence without a Caymanian business partner.

It seems to me the Immigration Monster would not be in a position to cause you any grief. I presume that you have been to the Brac and are happy with the prospect of living there. Is that so?

We loved the Brac when we were there, but we plan to go back to the places that make our "short list" with more of an eye towards living vs vacationing. We also intend to rent rather than buy real estate, so that we have more flexibility/mobility.

(in case you're interested, the short list so far also includes Belize, St Croix, maybe St Lucia, but still very much in research mode!)

Thanks again, you're a great resource!

I loved Grand Cayman. Divers paradise! Locals say you need to get off the island (fly) once per year. This may be true, so many destinations just a short hop away. I found the warmth of the people phenomenal. The safest place to be as many locals shared with me (this learned 13 yrs ago. Recent posting by Gordon Barlow says the Caymans do have some crime now, sad to say) Still the beauty is astounding. I loved the feeling of true relaxation there.
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Good luck with your choices!