unless you are set mainly on a cruise consider Beaches Resort Turks and Caicos> http://www.beaches.com/main/tc/tc-home.cfm Great family resort great diving, Scuba included, even the dive gear (although I always bring my own gear).
Two dives per day plus some pay-for optional dives. Other then that I would take option 1, Key West is hard to beat and I like the Bahamas better then Jamaica.
BTW, would you like to adopt me? DAD?
Enjoy!