I can comment on your second question, a few years ago my parents, aunt and uncle (all in their 70's) sister and BIL rented a villa at Leverick we kept our sailboat in a slip at Leverick for that week. We took the entire family out on day sails, explorered Virgin Gorda by a couple rental safari trucks, dressed up as pirates for the Leverick Jumbie BBQ, sailed to Scrub, they ferried back to VG, toured Tortola via guided tour bus. It was a wonderful vacation.

Tony