Pops...welcome aboard! Given what you've said so far my opinion is:
1. I would drop the nonesuch from the list. Nicely built, easily handled boats but really not a great fit for the Chesapeake wind conditions.
2. Add the Cat 30 back in if you're sure the dock depth AND approaches are OK for it. It is a really nice bay boat, cheap to buy and maintain, good factory support and enough room for your intended purpose.
3. You also might want to take a look at the Bristol 35's as they are lovely boats and the centerboard version only draws 3'9".
Overall though, I am reluctant to tell you to go look at $60K boats given your experience and lack of certainty that you will enjoy what you now merely anticipate. For this reason I'd advise getting an older production boat in the 30ft and under $20K range until you are sure what you want and need in a boat. While the Cat 30 would be my choice in this range, there are also plenty of O'day's, Irwins, Hunter's, Beneteaus etc. that will suit you just fine as an INTERIM boat. Since the depreciation is not a big concern on these older boats, you can't lose too much on a trade-in later on and later on you'll know a lot more about what you want and don't want in YOUR ultimate bay boat.