I used to take my old school SLR for the first few trips to Jamaica. Those shots remain my best. I stopped dragging that lumbering beast when decent point and shoot cameras came out. Now, I use a Canon S100 and I too have a waterproof case for it. Worked swell last May!
As for risk, here's a story from my first trip in 1984. We stopped at a barrel jerk spot at a residence on the West End Rd. We made absolute pigs of ourselves and they let us sit and eat in their front yard. We left and stopped at another restaurant to get some veggies to go with the salad. We ate two more meals and had dessert, too! By now we were ready to burst and drove back to our room at T-water. We no sooner got there when I realized I had left my camera and bag back at the jerk spot. I jumped back into the car and sped to the residence. IAs I got out the chef said, "Mon, you left your camera" and ran into the house to get it. I was very grateful and showed my deep repsect.
I'm not suggesting that you can leave a camera kit just anywhere and retrieve it, but I don't think Jamaica is any less safe to travel with our expensive toys than right here in the USofA.
Cool runnin's --Marblehead