We spent a week in TB in April, and absolutely loved it. Much more laid back than Negril. Can't answer most of your questions,
but you need to stop for your case beer before arriving in TB. I couldn't find it anywhere. In fact I would stop for all supplies before TB.
On the trip from Mobay - stop at Border Jerk up in the mountains - best jerk I've had so far in Jamaica.
Don't miss Eggy's bar on Frenchman's Beach. If you like Pelican, you'll like Eggy's.
We didn't eat out all that often, but a couple of places worth mentioning are Frenchman's Reef, and right across the road from Frenchman's is Diners
Delight. Great meals for about $500J, and nice outdoor dining area. Also, Pardee's has a great omelet for breakfast.