We have gone with Sunsail/Moorings for much the same reasons. We got a Sunsail (Jenneau) 36' mono in 2008 which was based in St. Vincent. It was an unsold and heavily promoted boat that had already started charter service. We had not been to the southern Caribbean, and we actually didn't see or use our actual boat until about 2 years into the program. When the St. Vincent base closed our boat was moved to Grenada then St. Lucia.

We sailed all over with reciprocal use, and were overall happy with the arrangement until phase-out neared and with soft demand for smaller monos, Sunsail didn't even want to offer to take it in trade and when I pressed them they offered something rather on the insulting side.

With a 1-year extension on our contract, we phased out after six years and moved the boat to the BVI (Conch), where we got some experience with the more typical charter arrangement (no reciprocal use, portion of actual revenue, payment of all expenses).

Although I was present at phase-out and did my best to get Sunsail to attend to all the contractual maintenance items, there were multiple issues that went undetected by myself and the surveyor and ended up taking months to track down (electrical mostly). At the time, Peter Twist at Conch lamented that the experience gave him pause to ever take over another boat from down island. The perception in BVI is that the service facilities and standards are better than in the southern Caribbean.

After two years with Conch, we sold the boat (which was subsequently lost to Irma).

Another two years, and we got the itch again and decided to get a Leopard 40 through Moorings and start the process again (and are leaving in two days for our first cruise on our actual new boat). Since the BVI had become our favorite destination, I would not have considered another base ( I could have saved $25k to take the same boat in Belize). Although we enjoy reciprocal use ( and have already re-booked some previous places like Tahiti and Australia ), I do want to see and use my own boat more often and keep better track of it's upkeep.

Hope this is of some use.