I started chartering in 1995. First in the USVI, then the BVI.
Most recent first: Pro Valor, w/Jim and Cecelia (there's a guy who sold the company trying to charter under this name also): 4 times, TMM, more than 5, BVI yacht charters 1, Catamaran Co 1, Sunsail 1, Moorings 1. Pro Valor worked the hardest for us, finding boats to meet our time slot. That's why we did our last 4 charters with them. TMM, also on the 'good' list. In the end, it is more than who had the newer boats, it was the feeling that you had the company working for you.
We now own a catamaran (not for charter) in the islands and as an owner i'd lean towards Pro Valor as my first choice for a charter operator to manage my boat.. PM if i can help. Joe/Ocean City/St John