If money is no issue, go with the top end companies Moorings and Sunsail. Generally they have the newer boats and know how to maintain them with full time staff.
If your going with one of the others you still have a great chance of a No Problem Cruise. While older and some may have more dings and a few non critical systems conditions, they are typically manageable and cost are typically lower particularly in the off seasons. With the older inventories they often give more days for the $$ occasionally double when they have boats on the docks not reserved. Just look at Conch Web site about this time of year.
Depending on which location your going to pick up a boat, I would also recommend you getting your own provision. If you do the standard full provision order you will end up having half the stuff still on the boat when you return. Of course I personally like it! Because I get the know some of them and they give me the excess! My liquor locker is typically filled and overflowing.
You can add to provisions at a lot of locations as you sail in the BVI. Some opportunities exist where a boat will bring them to you such as around Norman Island and parts of Peter Island by the supply boat out of Nanny Cay call sign Deliverance. Those that don't hear banjos strumming at that name will recognize it as a mini-market on a keel.
I prefer a sailboat to a motorboat, and it is my belief that boat sailing is a finer, more difficult, and sturdier art than running a motor.... Jack London