For mid-week provisioning, I use Dolphin Market in Cruz Bay. it's a short walk from the NPS dinghy dock and it's usually well stocked. They also have ice.

There is a a fuel dock in the Cruz Bay creek near the NPS headquarters. I've been seeing lots of boats going in there in the past few weeks. I'm guessing they also sell water.

I don't bother trying to tack upwind through the Narrows. Once you get to Whistling Cay, just motor to Leinster Bay or until you pass East End Pt. There you can roll out the jib and sail to Coral Bay or Ram Head.

I leave the CYOA base 3 hrs prior to STT departure. Last Friday, it took our friends 1 hr to get from AA checkin to the gate. They got to checkin 2h45m prior to departure and said the line was just starting to get long behind them.

It's hard to beat the convenience of Paradise Car Rental - no overbooking of cars like Avis or Budget or waiting 30m-1h waiting for your car to show up. Budget does have a downtown office for dropoff that is about 15 minute walk to CYOA.