J37 or Sabre 38MK1
I guess I look at this a little differently than most folks. The Sabre''s are really beautifully finished and have joiner work that knocks my socks off, but when I get on deck, I am always amazed at how poorly set up they are as sailboats. It drives me nuts that a boat that has a reasonably good hull would have a deck plan that is so poor for sail handling purposes.
To me there is nothing worse than to have to deal with bad sail handling gear. This is far more of a problem on a cruising boat than on a race boat. On a race boat there is lots of crew and someone named ''Moose'' can step in an ''muscle'' a bad situation back into line. But cruising you are shorthanded and have to rely on your own resources when the weather turns dicey or the winds go light.
To me the ultimate luxury is a boat that sails well and is easy to handle and so I would take the J-37 hands down, especially with a family along. With proper gear like the J-37''s, a child can actually participate in sail trim (when they get a little older) and the other tasks involved in sailing the boat.
There was a Farr 11.6 (Farr 38) supposedly in very nice shape for sale on the Lakes not all that long ago. That would also make a great choice for a performance cruiser.