Your check out Captain will know that your BVI plan is not a good one. Dropping off in another country without checking in is naive, illegal and not a good plan anywhere.
I have sailed US/Canada waters often and know they would not allow dropping of someone in another country that way.

You do not have to get him ashore at a 'port' -- I have been that check out Captain a few times myself, and would suggest Maho Bay STJ as a much easier drop off point for your itinerary. Closer to the road and Much! easier to get a ride to Cruz Bay. About an hour motor up to Leinster Bay afterwards if that is what you want to do, NPS moorings in both places.
Take every advantage of the knowledge that your captain can impart -- on the vessel systems, the boat handling, the rigging for raising, reefing and dropping sail, safety concerns, navigation suggestions, mooring pick up practices, dinghy operation and handling -- but particularly the vessel systems for power management, system operation and maintenance and troubleshooting.
It is a huge bonus to have a knowledgeable sailor familiar with the vessel, waters and in this case Rules, on board to start a charter - it will give everyone on board a chance to ask questions that would only distract you as Captain of a new boat in new waters the 1st day.
Any charter company that sends a vessel out breathes a great sigh of relief if a Check Out captain is aboard for the 1st day -- it greatly increases the probability of a successful and trouble free charter for ALL involved and will make your job as captain for the duration considerably more effective and [hopefully] stress free.
FWIW
This all is only my opinion - except for the BVI drop off - from my experience of decades on every level of chartering from being a guest, crew, employee and Captain
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