I think the Judge is finished much nicer. I also like the fact that they are now wood free, have higher head room in the pilothouse, uses a little nicer hardware, and are local for customer service. I have spoke with a couple of owners, mega-jack here being one, and they do nothing but talk about how they take care of them after the purchase (have heard the same about Maycraft as well -- havent had any issues myself to see). I also think they are a bit more pleasing to the eye than the maycraft. I really wanted a 27 Chesapeake last summer but couldnt bring myself to spend 15k more on the boat. They are so close in layout and design that I wouldnt have had anymore fun or gained any additional function for the extra dough. They are also very close in size being the MC is a very long 25 at 25'6" and the Judge is only 26'4". I do think my maycraft is an excellent, well made, tough boat and a better deal for the dollar. However, the Judge is just a little nicer boat IMHO. (I actually think May-craft is about the best boat for the buck though-hense my purchase) The things I like better about my May-craft (aside from cost) is the 8'6" beam so I dont have to worry about a permit to tow, there was some water coming onto the deck on the 27 judge at the annapolis show in fall 04 with 4 adults in the cockpit--my floor has never had water on it despite having a full load many times, full platform on my bracket, and the fact that I didnt have to wait for it to be built. When I bought my Maycraft I really wanted the Judge 27 but narrowed my choices down to the 2320sl Parker and the Maycraft due to cost. Layout was deciding factor. I am still happy with my choice.
BTW, I dont work for Bill...I didnt even talk to him when I was shopping (spoke with a salesman named Dennis). I am in the printing and directmail biz. I am just an admirer of the boats.
on another note, I would love to see an anderson one day. I didnt even know of them until after I decided what boat I wanted.
I'm no expert, but a neighbor of mine has one for sale (it's probably listed in the Annapolis paper) and it looks sweet. It's an Eastern - 19-21ft, dark blue hull with a 90-115hr 4 stroke Honda. Good luck.