Paul,
Judge boats are well respected by the local waterman. I was at the factory last summer while looking for a boat and seriously considered the very boat you're talking about. Bill Judge does a nice job with his boats. He will work with you to see you get what you want. His operation is a small personalized one. The Chesapeake can be alot worse than the ocean because of the shallows and currents. I've come to find that out first hand after moving here from New York. As far as performance, you should have no problem. I think you should direct that question to Bill Judge himself. He will be upfront with you. As far as a 26', I don't believe he makes a 26'. By the way, the only reason I didn't buy was because the cabin was not big enough for the admiral. I was looking to get a diesel inboard. Another good builder in the same general area as Judge is Glass Boatworks. He builds only custom and mostly for the watermen in Exmore Virginia. His boats are utilitarian but tanks. It's another family run business. His 28' is 9'2" wide.Here's his website and also pictures of the Judge 27' that was just completed while I was searching.
http://www.intercom.net/~boatwrks/ 
Judge Yachts 
