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Highly recommend you get a Virgin Islands cruising guide ahead of time. The most popular is the one authored by the Scotts, but the Pavlidis (Seaworthy Publications) guide is also worth it and--given the cost of your vacation--buying both would be reasonable.
If you haven't had a mal de mer problem in your home waters, you won't have a problem in the BVI--even to Anegada, which I don't put in the same category as ocean sailing. Except for the Anegada trip and going to weather on either side of Tortola, you won't be sailing very long before your next anchorage, so you can tuck in quickly if your crew start to get queasy. As someone else mentioned, the clockwise route is probably preferable because you can break up the windward slog into smaller pieces.
We've taken a slip several times at Spanish Town (Virgin Gorda Yacht Harbor). It is an easy reprovisioning stop, has showers, and you can refill your water tank. The slip fee is very reasonable IMHO, and even for a 42 ft boat was only twice the typical mooring fee. We have used this marina to make a landward approach to the Baths and avoid swimming in from the dinghy tie-up there. We always treat ourselves to a sunset dinner at the Top of the Baths restaurant--it is only a little pricier than, say, say the Cooper Island restaurant, but very reasonable for the noteceably higher quality of food and service.
Some logistics issues: You need to bring your own mask, snorkel, and anti-fog gel, unless you want to take your chances on a poor fit. You should be able to live with the fins provided by the base.
If you like to get rid of the salt after the daily swimming events, you should plan on replenishing your water supply once you've been out several days. I've already mentioned Virgin Gorda Yacht Harbor at Spanish Town, but you can readily get water at several facilities in North Sound, such as Saba Rock, Leverick Bay, Biras Creek and Bitter End. Another water stop is at Marina Cay, which also has an OK Pusser's Restaurant. Check the guides for others.
Depending on the charter base fees for a first night aboard, you may find an overnight ashore is cheaper (and more comfortable) if it is only for a couple.
Having the charter base provision is a real convenience, especially after your long trip, but you'll have to live with the inevitable surprises. You may not save enough by provisioning yourself to justify the time and energy it takes.
Regarding charter bases: We've chartered from a couple of places on Tortola, but it's been quite a few years. We have since migrated over to Island Yachts at Red Hook, St. Thomas for our most recent 6 or 7 Virgin Island charters, but that's another story. You may want to charter out of Tortola for the first time in the BVI to avoid the extra complication of checking in and out of customs and immigration as you go from USVI to BVI waters and back. You'll also maximize your time in the BVI--7 days goes pretty fast, so you might consider a 10-day charter, if your time and budget allow.