Hello Fellow Travelers!
Yes, summer is fairly cheap in the Caribbean because that is hurricane season there. You probably won't see one but if it does happen, it can cause massive damage like on Grand Cayman some years ago.
A problem with the islands is that generally they are sun, sea and sand and little else. A friend of mine who likes that got fed up on Antigua after just one week (of two).
Every island varies. I would put Jamaica as potentially dangerous. Then again, people on other islands have been murdered for small sums of money, because they have interrupted a burglary and such.
I am not trying to put you off but warning you that there is more to the islands than nice beaches.
I would not count on finding work as there is probably a queue of people for such jobs.
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