We are frequent Moorings travelers (powercat). As you suggest Wed to Wed hitting Anegada over the weekend. We also like Friday to Monday if you can swing a couple of more days.
This keeps us off cycle with the other boaters to the harbors. We usually do sleep aboard but get down early enough and have a great relationship with base that they let us out that evening. We are on the DCA - SJU - Island Birds to EIS flight and the DCA to SJU flight gets us in around 12 noon. Dont know about that TN flight. Some of our crew did the MIA EIS flight.