Thoughts on a mid size cruising boat
I just did a quick "Yachtworld" search on 32-36 footers in your price range the MidAtlantic region, (MD, DE, VA) and hit on 76 boats, including relatively new (early-to-mid-1990''s) Beneteau, Catalina 320 and Hunter 336 models, as well as older Sabre, Erickson, Pearson etc. etc. You are in good fishing grounds to cast that "wide net" over a wide selection of boats.
I sail in the Pamlico, and the cautions on draft are important here just as in the Chesapeake. I''m owner of a Catalina 34,(shoal draft!) and based on your desire for comfort vs. speed, the cockpits and accommodations on the newer Hunter/Catalina boats may help you with the First Mate and the kids. Also, since there are so many around, and the factories are still turning out boats, support and advice is probably going to be easier to come by.