Re: Buying our first sailboat
+1 on centerboard boats being tough for starting with a (young) family. It can be done, but probably a better idea once they can all swim. Rogue wave or puff in inexperienced hands, and everyone swims.
What makes it tough is we'd be hard pressed to give you a sailboat that isn't a centerboard that you can fit into the bed of your pickup, that would be stable for the whole family.
If you have to car-top or truck bed it, then light 12 footers would work to learn on (zuma, snark, escape).. but they aren't real big or comfortable for several people.
If you move up to trailerable, then a stable keel-boat is a great starter boat for a family, like a Com-pac 16, or West Wight Potter 15, or a Precision 16, or keel- centerboard boat like a Catalina 22, or Precision 18.
Another option that is an easy starter is a cat boat, and something like the com-pac picnic cat might be an option, but you'd still need to trailer it.
Hull #68 S2 7.9 on our little landlocked puddle, Lake Wallenpaupack, PA, it's cheap, trailerable, and paid for.