Sailing out of Annapolis, I went through almost the same search (except a third of your budget) when I bought my 38 foot boat last year. The Chesapeake is great at setting up this kind of conflict. With all of its wonderful anchorages it is always nice to have a little more speed so that you have a bigger sampling to cruise to and with its prevelence of light air, a high sail area to displacement ratio means a lot more sailing days and a lot more sailing time in a season.These larger sail area to weight ratios places a real premium on high quality sail handling gear for the ability to easily depower the sails. Unfortunately, that typically means that the traveler will end up in the cockpit. While the Chesapeake rewards boats that have comparatively shoal draft (7 feet or less with less than 6''6 being more ideal), the ability to carry a larger sail plan somewhat encourages deeper draft.
On the other hand the summer conditions places a demand on good ventilation below and a comfortable cockpit above. Unfortuneately many late 1980''s performance boats have comparatively poor ventilation.
As a result there really are comparatively few boats out there that really meet your needs without some compromise. My wife and I very much agree with your husband about the traveler in the cockpit. She was concerned about the high sheet and traveler control line loads that cabin top travellers imply and felt that she wanted a boat that she could trim the mainsheet herself.
Here are a couple suggestions:
Beneteau First 36.7:
I know that you said no big 3 production boats, but these Bruce Farr designed performance cruisers offer a very high build quality, a nice layout down below, good all around performance, excellent deck hardware, and wonderful ventilation. There is a big difference in design and build quality between the ''First'' series and the Oceanis or ''number'' series boats that most people think of when they think of Beneteaus. I suggest that you keep an open mind on this. These are exceptionally good sailing boats and you should be able to buy one new within your budget.
Beneteau First 38s5:
This is an older First series 38. I have a lot of experience with these boats. They sail well and have an extremely nicely detailed interior. Most of these had the traveler on the cabin top. A friend of mine in Savannah is selling a clean one with a genset and air conditioning in the $115K range.
Beneteau First 36s7:
This model replaced the 38s5 and was replaced by the 36.7. They sail well and have an extremely nicely detailed interior. Most of these had the traveler on the cabin top. They are an awful lot of boat for the dollar and make good bay boats as well.
Dehler 38 (Nova):
Although pretty rare in the States these boats offer excellent build quality and very good performance. The are typically pretty shoal draft but lack ventilation.
Dehler 36:
These are pretty rare in the States and are at the outer edge of your price range but would be an excellent choice for your goals.
Express 37:
These are great Chesapeake Bay boats in a lot of ways. They are not as ''yachty'' as the Sabres but are extremely well constructed and offer excellent all around sailing ability. If you can find a ''C'' or ''MkII'' model they had an aft cabin layout, better vetilation and a bit more plush interior.
Hanse 371: These were almost designed to order for your purposes. Classic good looks (although something of a modern interior design), well constructed,Good ventilation, excellent performance and a price new that is within your budget.
J-110:
These are pretty rare boats but offer a lot of modern features in a genuinely dual purpose boat.
J-37C: These are nearly quintessentially ideal bay boats. Good all around performance, good ventilation and comparatively shoal draft bulb keel models.
J-39: These are comparatively rare models that had a second life as a J-120. These are a bit more race oriented than a J-120 but offer a nice combination of racer/ cruiser at a price substantially lower than your budget. The cockpit is something of a compromise and a lot of these were set up with headfoils and not roller furlers.
Tripp 37

Holby)
Beautifully built, very nice design, a little deep and a little short on ventilation.
X119 (39 ft): These are very nice performance cruisers that offer a nice combination of accomodations and performance.
X412 (41ft): These are similar to the X119 but are a later model and more cruising oriented. These are beautifully constructed and detailed, nicely finished boats that offer a lot of performance.