Re: Champagne taste on a beer budget
First of all, your dream boats are not particularly well suited for the Chesapeake. You really need a boat that can sail well in light air and is shallow draft for gunkholeing.
Second, where will you keep the boat? And what will that do to your budget?
Find a slip you can afford, then find the boat that will fill it and let you actually sail in light airs. You will rarely be out in a ful-fledged storm and in the Chesapeake you are never that far away from a safe harbor, so you don't need a boat designed for the North Sea, just a good all arounder with the accomodations you need.