Big up! Email Owen - you won't regret it!
Great tips @Iowa.
"Food budget is up to you" - a good one, and also very subjective. Personally, my wife an I ate like kings (some days) for about $50 per person. In Jamaica, eating like a king isn't defined by the price of the meal but rather the quality of the food and cook. One day we got a lobster dinner for 2 for less than $40 at 3 dives (there was a special) and it was one of our favorite meals. Ask around. There are great deals everywhere. The side of the road jerk places are my favorite. I can't get decent jerk here, so $5-10 for a good jerk dinner is eating like a king for me.
"Rick's and Margaritaville are the worst values" - I didn't dare venture to Margaritaville. I did try Ricks and, out of 28 days in Negril, it was the worst experience and a complete waste of money. If you want to "see" Ricks, catch a catamaran and view the tourist trap from a distance. Otherwise, expect to eat a TGI Friday's or Chilli's style dinner for 25-50% more than a comparable meal in the USA.
"Tip like you are a little crazy" - yes, I couldn't agree more! Don't forget about the hotel staff and taxi drivers. If you are in Negril in the off season, tip even better than you normally would (when deserved).
Thanks for the great tips!