re: Jamaica. Is it safe to leave the resort?

If you want to leave the resort, book a day where the taxi can take you on a few planned stops.

Our day consisted of the taxi taking us and a few others to the duty free shops (which were surprisingly nice), ending at Rick's Cafe at sunset. The driver sat outside the spots and had a meetup time for leaving.

On your way to these destinations, we rode through the slums and were enlightened as to why we made a good decision not venturing out alone.

The hassling is bad enough on the beach, I couldnt imagine being out there on the streets alone.

ETA: I stayed in Negril - Sunset at the Palms. Forewarning, 7 mile beach is not private. You will obviously have people peddling drugs, and you will have women trying to braid your wifes hair, sell you Bob Marley paintings and other shite. Prayers sent if you run into King Louie.