I travel by myself to negril a lot (I am not a guy though!). I book where I am going to stay by the qualities of the place I am staying and what I want and the budget I have -kitchenette, beach, cliff, pool, no pool, food, bar, fridge no fridge etc. Then I go from there to where the party is--three venues on the beach with parties different nights, the jungle, etc. I always meet people at those places. And there there are the webcasts as well. I don't try to book my accommodation based on what kind of crowd might be there--sometime in off season there are barely any guests at places. I would say have him stay somewhere central on the beach (not tucked away up in an AI) and make sure he has the negril map and a list of the parties, etc. If he is feeling a little shy, a rum punch can do wonders. Also make sure he has an idea of how to get around. Or even better, if he can save a little money by staying somewhere like Bar B barn, maybe he could have a go-to driver guy that can take him around. If he is on the beach it is fun to bar hop and check out the vibe at different places. My first trip I stayed at Samsara and took their shuttle to the beach and walked the beach a lot, met a lot of tourists and locals, went to parties, and towards the end of my trip met a few girls who had checked in to Samsara hooked up with me and we went to a show at Bourbon beach together. I myself don't like to split my stay unless I have a couple of weeks--it takes valuable vacation time to check in and out--pack- unpack.