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Your best bet is to correspond in writing and get your replies in writing. That does not mean they are legally binding but means they may be correct and any penalties (but not fees) will probably be waived if they are wrong, but you affected in reliance on them.
"Additional reporting and entry requirements may be obtained from the U.S. Customs Service, Office of Field Operations (Attn: Passenger Operations Team), Washington, DC 20229. For additional information on legal requirements, contact the U.S. Customs Service, Office of Regulations and Rulings (Attn: Entry Procedures and Carriers Branch), Washington, DC 20229."
I would suspect that you would have to physically remove the boat from the state where it was purchased (typically withint 30-90 days) in order to avoid paying state sales tax on it and to avoid mandatory state vehicle registration.
If the BVI will issue documentation/registration to an alien, that's between you and them, but you would want to contact the US federal offices above to find out if you are eligible for a cruising permit if you are originating from within the US--a opposed to entering it from sea. Everything on their web site is predicted upon entry from outside the US.
Or, you may wish to employ that firm in the BVI as your agents and ask their experience on this. The situation is unusual.
You will find the Florida motor vehicles offices and sales tax offices have web sites. They explain that a non-resident, who purchases a boat in Florida and then takes it out of the state within 90 days, does not have to pay sales tax on it at the time of sale. A broker would normally collect sales tax, an individual seller would not collect it, relying on the fact that you would pay it during state registration. We use the termn "registration" for state registration only, and the term "documentation" for USCG titling for US citizens only. There is no federal registration per se in the US.
Again, you would need to check with the Caymans to find out about registration for an alien, whether you might need to form a corporation, and how you would renew your status from outside the Caymans. If you purchase the boat in Florida and promptly leave, I do not believe you need the cruising permit but again, as an alien originating your purchase and trip from within the US, rather than entering from the seas, you would want to check with the US offices cited above.
You could get caught in limbo, if you were stopped trying to leave the US without proof that you had legally entered it with your boat. The USCG or US Customs should both be able to answer that, and if their answers are at all different--try again.