My wife and I just got back from a charter on a 38ft mono from DYC. Similar situation to you...normally go with a large group of friends, but the group wasn't available this year and we decided to do our first trip as just a couple. Went great. The 38ft mono was the perfect size for just the 2 of us and we got a great price as well. Was a completely different vibe than going with friends, and definitely one of our best trips ever. No issues with a mono in the BVI, including at Anegada and anywhere else we wanted to go. My wife isn't a huge fan of the heeling, but I just sheeted out and reefed as necessary to keep her comfortable.

Sean