(This will require several posts since this BB only accepts short answers.)
You have an interesting set of objectives. Like I said, you have to know what someone wants out of a boat to know what is the right thing to say sometimes. (Sail a couple tacks in their topsiders so to speak) I know the Rock Hall/Gratitude area. I''ve sailed out of Annapolis for the last 18 years and we
anchor up in Swan Creek fairly often. One of my favorite cruising spots is just around the corner in the Chester River. Which has little or nothing to do with your situation.
I think that if I basically understand what you are saying, you are looking for a boat that is comfortable for weekends and which is a "quality boat". Of course the term "quality boat" means different things to different people and in different climates and sailing venues. In other words, a quality boat for sailing in New England may not be a quality boat for sailing in the Topics and a quality offshore boat can make a poor quality boat for the Chesapeake Bay. Or in other words still, when sailors talk about quality in boats we all have our own ideas about what are the elements that make up high quality.
(To be continued)