Are you staying in a unit with a kitchen and cook service? If so, we like to stock up and have them cook us breakfast. We like to get supplies on the way in so we have what we need for the first few days. Either MegaMart in Montego Bay, or last time just stopped in Lucea.
We've used Leon a few times, he's one of their drivers. Nice enough guy, a little more expensive than some of the independent drivers. We've used Ashton Pitt our last few trips. Leon did question why we didn't use him, we just told him Ashton was cheaper and he let it go. For short trips, usually one of the guys is hanging by the front, I'll use make them a reasonable offer and they will usually take it. If not, it's easy enough to find a taxi on the road. I've never had a problem getting a ride back from somewhere.
For us, we usually grab lunch from one of the vendors, jerk pork, patties, etc. There is usually a jerk guy set up across the street as well. Rainbow Arch two doors down is also good.
We've done Club Mobay a few times, I think it's worth it to guarantee you won't be waiting in line for an hour or two, but it's a gamble.
For dinner, we prefer restaurants on the West End and it gives us something to do for the evening. LTU, Ivan's, 3 Dives to name a few.
The ATM at Time Square usually works, it's walkable. There is a cambio right there too at the entrance to Bourbon Beach.