Re: Abacos or BVI
I don't have any experience with CYOA, but I've found a qualitative difference between the Island Packets and the typical Beneteau/Jenneau charter boats, having chartered from Moorings, Sunsail and others besides Island Yachts. The Island Packets won't appeal to racers, but may be more suitable for the kind of sailing you have in mind.
If you compare pricing, you'll find some differences among the charter companies, like 6 nights instead of 7 for a "week's charter". You might also consider the cost of an overnight on the boat before the charter starts.
If you are considering a USVI start, Red Hook is more convenient to St. John than Charlotte Amalie, but it isn't a huge difference. Charlotte Amalie provides the duty free shopping and local vendor scene and is closer to the airport, however, but then you'd miss the taxi ride to Red Hook, which provides an introduction to the island culture and topography and some nice views.
If you are going to St. Thomas for the first time, you ought to stay overnight in a B&B style hotel in the Charlotte Amalie area and check it out.