Some very thoughtful input already from folks far more familiar with the lay of the land than me. I'd only add a thought. If staying close together is of high priority, then you may have difficulty in some of those anchorages (as already noted), whether BB or otherwise. Assuming you don't roll in at 4 pm, you'll be fine at Norman and Bitter End. And though you'll likely both find balls at the other stops on your proposed itinerary, you may find that difficult. If those destinations are important to your planning, then I'd say go for it...provided you assume you may not be neighbors with your mates. Otherwise, it might be a great opportunity to consider some of the other suggested anchorages where you will almost assuredly be able to stay close: Little Harbor JVD, Diamond Cay, Marina Cay, Great Harbor (Peter), and the like.

Tough call. We've sailed in random with other boats 3 or 4 times, and we've always valued being able to pick up balls more or less side by side.