Have you talked to the TUI (Sunsail fleet owning company) about the tax position? There are any number of US citizens with US flagged boats here in the Tortola Sunsail and Moorings' fleets, and I know that Moorings (who are now combined with Sunsail in the Tui empire) have, or used to have, an extremely active Owner's Group. The guy to talk to would be Michel Bennarosh at Sailonline dot com. There are ways of doing it but as I recall
, it depends on if the taxman considers it an "active" or "passive" business (I think those were the terms!). Being in an actively managed charter fleet makes it a bit difficult to assert that you
are the "active" one: I think you have to do a lot of marketing
and promotion yourself to make you"active".
One hint about having a boat in the fleet. Get to Know the staff at the Tortola Base - in particular, Robert, the Technical Manager!!
best of luck, Tony