It Depends
How deep is deep. I've been sailing with a 5'-6" draft for quite a few years on the Chesapeake, and find it to be no problem. A friend finds 6' to be just fine. There are plenty of places to go even with a deeper boat. The performance of a deep keel will always be better to weather, but a winged keel Hunter may be more weatherly than some older deep keeled boats. As I said, it depends on the design of the boat. In my opinion, 5'-6" is about as deep as I would go for the Chesapeake.