We don't own a boat but have been chartering with Horizon for the past 17 years, 38-47 foot monohulls. Usually 2-3 weeks each year. Great people to work with. The guys doing the 2 hour checkout (before you leave the dock) are very thorough. All systems and rigging are explained. Years ago I asked one of the guys how he could tell about the competency of the captain without regard to the resume. He smiled and said, "its all about the questions during checkout". My quess is you will head out to either Norman or Great Harbor on Peter and demonstrate the skills necessary. They frequently pull a second dingy behind the boat to make their way back to Nanny Cay if you "pass".
All their boats have the operations manual on line. You should go though it.
Given your ferry arrival time, do you plan on overnighting on board? Because by the time you get to Nanny Cay it will be 4:30 and that does not leave sufficient day light to sail out and demonstrate your competency.
We have sailed for three weeks and never needed to refuel. You will need to take on water a few times with five people on board. Thats where the docking ability comes in. BTW, there is usually good help at the fuel docks to secure the lines. If you can get close enough and can throw a line far enough, you will be fine! Best of Luck!