Get to Cooper early, it fills up quickly. Should be there by 2 PM. Also get to Anegada by 11 AM. You should have no trouble finding a ball in the other locations (Saba/BEYC, Trellis/MC, CGB, Norman). You may not find a ball in White Bay on JVD but should be able to in Great Harbor. Fall-back locations would be Great Harbor on Peter for Cooper, anchor in Anegada (you'll be fine), Little Harbor on JVD is never crowded and has some good restaurants (we like Abe's). You didn't say whether you are planning to eat out all the time or cook on the boat sometime. If you plan several meals on the boat, use that as your flex tool in case you have to discard a location where you were planning to eat out and instead move to a location that has no restaurant. Obviously, being flexible is necessary. You should be ok with the 10' dinghy, just go slow especially in choppy water.