Welcome to Sailnet!
As for introducing kids to sailing... There are different issues here. If you just want to "introduce" them to sailing, then a comfortable family boat is a nice way to go. But if you want to teach them to sail, I cannot recommend strongly enough that you get a sailing dinghy to tow behind the mothership. You'll want a dinghy anyway for gunkholing the Chesapeake -- might as well be a teaching platform for the kids too.
P.S. Your background story brought back memories -- my very earliest sailing experiences were in MWR sunfishes.