I've gone to all-inclusive a couple times (once in Mexico and once in Barbados). Both times I got really good deals, so I didn't mind going out to eat at other places some of the time.
In general, I wouldn't do an all-inclusive again unless I got another great deal. I like to explore and try local places, so it's not worth it to me.
Jamaica might be worthwhile, as I know some areas are not the safest, so it might be nice to have a guaranteed "safe" zone. I guess you could say the same about Mexico, although I wandered around there and never felt unsafe (Playa del Carmen, super busy and super touristy and Loreto on Baja California Sur which is the anti-resort.)
Barbados is another island I enjoy visiting. There are lots of great restaurants and sites / activities you can organize on your own though, so I don't think an AI is the best option. Maybe somewhere that offers breakfast instead? The last two times I went there, I stayed at a small, local hotel though.
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