Rob, where in the Caribbean were you born? I assume it was one of the USVIs, but that's not a sure thing, I know. I'm sorry that your father had such problems in the Caribbean, but he might have been more exposed to theft as a resident carrying conspicuous amounts of money.
We have been going to the Caribbean for 30 years, still own an apartment on the island of St. Martin, and lived and cruised the entire eastern caribbean chain in the late 80s, early 90s. We had an anchor stolen in St. Martin, but I am pretty sure it was another cruising yachtie that stole it (well, Peter might have lost it after he buoyed it and left it in the lagoon for several weeks).
With regard to crime, I would say that the USVIs have the worst crime problem in the Caribbean. There is no place in the Caribbean (except for Colon, Panama) that I did not walk alone. I also think that, due to its success as a tourist destination, the Caribbean probably has a greater incidence of petty theft (purse snatchings, pockets picked, etc.) than other places, though we did not experience such problems; we probably didn't look as if we carried enough money to make it worth it to try to steal!
However, petty theft is not, in my opinion, an excuse to carry or use firearms. But if you feel better wielding a shotgun whenever a friendly fisherman approaches your boat, that's your choice. But do read my friend's report of a piracy attack in Indonesia, at http://www.cruiser.co.za/hostmelon39.asp