Judging by your resume, the check out likely will be a non- issue. Take it as a time to get use to the feel of the boat.
Ask check out skipper to let you get the feel of maneuvering to pick up ball . See how it moves as you go into reverse.Figure eight turns etc.

Perhaps plan first night stop at Trellis bay as plenty of balls(no rush to get there) and can likely disembark. Hopefully you have a water maker and if so, no reason to dock until returning to base. Likely base can send out a driver to assist you in coming in... One phase to keep repeating in your head (and out loud) is "SLOW is PRO" , around mooring balls and docks.
If no water maker, then you will need to dock for water, but a T-Dock... Remember which way the boat walks in reverse? Refresh on purpose of lines (bow/stern and Spring lines). Know the draft of boat and whether Anegada not recommended for that particular depth. You can have great time even if you skip Anegada this trip... and an excuse to come back soon.