Not sure where you live, but a yr of sailing out of Windworks, or Seattle Sailing on different sized boats could be good for the both of you to decide what style of boat would work best for the two of you here in Puget sound.
I'm in Magnolia (just barely). I'm aware of SSC and Windworks. Windworks' price structure seems appealing for occasional use; SSC's for more frequent sailing. SSC's fleet is mostly J's, and with the wife and kid onboard I'll need to be on a boat that's more cruiser-oriented. Whatever I do will likely need to wait until spring. I keep bouncing back and forth between a newer, spiffier 25' or a larger albeit older/more basic 28-30', the thought being that a larger boat would offer more motion-comfort for the wife and kid.