One more thought:
My above suggestion was aimed at your haul-out/storage needs for the winter of 2009/2010.
As for making the Chesapeake your sailing base next year, there may be other locations that are better for that.
For instance, Hartge Yacht Yard
in Galesville, MD (10-12 miles south of Annapolis) is a good spot for exploring the mid/upper Bay. They have moorings available which could bring down your costs a bit.
I'm sure you'll get lots of other good suggestions.