Re: Experience required to bareboat?
We've chartered with various companies in the BVI's including TMM. Our experience (yours may vary, and this data is a few years old) is that TMM gets slightly older boats than the Moorings and offers them at lower cost than same. This creates some additional risk of maintenance issues, and we've had some, but they generally do a good job. If you charter enough, you will experience a maintenance issue no matter what company you charter from. They are boats just like the ones we own, but used harder.
I recall on our first visit to TMM, they actually took us out for a test sail. We did a couple of tacks and returned to the dock. I remember thinking, good for them actually testing skill level independent of our resume which involved multiple cruising boat ownerships at that time. You see some pretty scary things done on charter boats in the BVI's, and most companies don't appear to check skill levels at all. Other posters are right, you can charter a boat in the BVI's with much less experience than yours.
I'd call them up at the base in the BVI's, talk about my concerns, and ask if you can take the skipper out with you for one day if all is going well, and volunteer that its fine with you if the skipper stays longer if it isn't. See how they react. I suspect they'll have no problem, and you'll be on your way after a day.