How big is too big to start out?
I have been sailing a Macgregor 22 for a number of years and would highly reccommend one for starting out. It has a heavy swing keel which is a lot more reassuring than a small dingy that is easily capsizable. It trailers nicely and launches just about anywhere off the trailer. I started out with smaller boats but moved up to this one for greater comfort level with children in rough water. (Someone out there mentioned they have one for sale.)