I agree do NOT get BIGGEST yet.
I routinely sail Lagoon 42 "single handed" (even with others on board. Good visibility Self Tacking Jib(i.e. no crew needed). Main halyard to helm with electric winch. Sport top, so direct view of cockpit. Of course A/C/ genset/ Microwave/ WiFi....
I also agree Moorings a "safe" choice, but not the best choice. Agree TMM, CYOA should both be way up on your list, but still a reason the bulk of charter companies are IN BVI, not near BVI. Charter customers mostly want to start in BVI.
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