chesapeake bay sailboat?
The Chesapeake really rewards lighter faster boats with more sailing days, more places to go on a weekend and more sailing time during your time on the water. You have a very strange mix of boats that your seach has "narrowed to" namely,"Island Packet, Aloha, Bristol, Sabre, Tartan, Endeavour" There is no pattern to this list. The Endeavor and the Island Packet make no sense if you''d, "like a boat that offers light air performance" and represent both ends of the quality spectrum. The Sabre and Tartans are good boats for the Chesapeake with good all around sailing manners and reasonably good build quality. Bristols fall in a category all of their own with each model having its own characteristics somewhat unique from the other Bristol models-some good and some really anachronisms. How the Aloha got in here is another mystery but they are closer to the Bristols than the other on this list.
If I were trying to find boats that meet your needs and are suitable for the Chesapeake, I would keep the Tartan and Sabre in your list and add;
Beneteau First 32s5
C&C 33 and 34
Carroll Marine Frers 33
Dehler 31, 34, 98
Farr 1020 (would be one of my first choices in this list)
At least that would be my first thoughts.
Bedtime, Good luck