I've gotten the impression that most thefts from hotel rooms were either crimes of opportunity, where a door or window was left unlocked or open, items are left in plain sight, etc. I've also got a theory that it's well known that the locks on many of the doors in Negril... well for lack of a better word, they suck. Staying in rooms that seem to be using $10 Home Depot doorknob locks is not terribly confidence inspiring, and don't look at the quality of the work that's been done installing them... I had a balcony door at one place where the screws in the latch were backed out half an inch, and the bolt would shift around in the jamb with just a tiny bit of pressure. I have no doubt that a good hard push is all it would have taken. What was really odd though is they weren't stripped - I had happened to have a screwdriver in my suitcase so I tightened it down and it was secure. How does it get that bad without being noticed? Or was it intentional? From some of the stories I have read (here and elsewhere) some people have claimed that theft from their rooms was an inside job...
That being said, I don't bring anything I would be upset about losing. The good cell phones stay home, and we bring cheap smartphones (I work in the industry so I always seem to have phones around) that get left behind with a friend or someone who helped make our trip memorable. She leaves the jewelry home, and I don't wear any but my titanium wedding ring anyway. We don't bring a fancy camera, because even an inexpensive smartphone has a decent camera nowadays. In the past, I would always bring the latest smartphones with me, and if I pulled them out they attracted a lot of attention, which I don't need. It's not overt, but you are being watched. If you have valuables like expensive electronics, and you take them out of your room, people notice.
Any cash or credit cards I won't need for the day stay in the safe with passports and other documents. When I know I'll be out for an extended time or need to carry more than just pocket money (for an excursion, a purchase, fancy meals, etc) I keep small bills in one place, and the bulk of my money somewhere else hidden on my person. That way if something were to go down, they can have a couple bucks and it's no big loss for me. If I need access to more money, a quick trip to the bathroom to get it done so no one sees. Also no flashing wads of cash / large bills when buying small items like a beer or food.
This is pretty much what I do no matter where I travel. As a tourist you can be an easy target if you allow it. This is good advice for travelling anywhere, not just Jamaica.
