Son-
I have a 2005 323 with the shoal draft keel and I would consider it maybe a little on the tender side, but not bad. I have been in 20+ knot winds, while racing with my wife, with full sails. Usually when cruising we use the first reef around 15 knots when it is gusty, which is most always since we sail on a mountain lake mostly, and the second reef around 20-30 knots. If we have guests, who are a little skittish, we just reef until they are comfortable. The dual reef lines back to the cockpit are great. We can throw a reef in under a minute on the main and the roller furling jib is just as fast. I think if I were to order a 323 again I would get the swing keel. The reasons being we occasionally race and the boat will probably point better, this is just an assumption since a straight keel usually points better than a wing or bulb. It points pretty well now, but a little bit better is always a good thing. For a cruiser the shoal keel is probably the better choice. The other reason for choosing the swing keel is it would be easier to trailer, around 2 foot shorter, and launch. Hope this helps a little.Sail On...Terry