Cape Dory 30
The Cape Dory is a pretty boat to look at. Very "Nautical", sort of a poster child for "This Old Boat". But I have to agree with Jeff, while a dandy at the dock, it would be a nightmare to do any serious sailing on one.
You would be better served with a much more modern interpretation of the "Pocket Cruiser". If you can go with a tiller, take a look at the J-30. While you instantly think "Racer" with any J-boat, these are really nice all round boats. With their fractional rig, smaller head sails, they are easy to handle short handed. They have a nice interior and can be had in the mid-$20k range. And they would sail circles around the Cape Dory, maybe even backwards, in every type of condition.
You should also take a look at the S2 9.1, the G&S design. Also a nicely turned out boat that is lightyears ahead of the Cape Dory design.
And also take a look at the Tartan 3000 (not the 30) a nice modern design that is well suited to what you are looking to do.
Any of those boats would also have a better "market" when it comes time to sell.
If you are looking for a pretty boat, something to polish and varnish and have cocktails on at the dock, the Cape Dory would make a nice conversation piece. But if you want a boat that will sail nicely on all points of sail, get you there and back with little fuss or bother, take a look at the three I mentioned.
I have pretty thick skin, so I can endure the slings and arrows of the "traditional" set also.
Good luck in your search!