Wow jphart - thank you so much for all that information! Frankly, I hadn't even considered a captain (since I've never wanted or needed one in the carrib) but you make some excellent points and it does seem like that would make a huge difference in stress.
Thinking back, one of our early trips to the BVI was with a flotilla and it WAS really nice to have the lead boat arranging all the shore activities.
This gives me much to think about - many thanks again!