Just buy the most boat you can afford. I myself worked my way up from a a 21 foot Switzer, to a 24 BAJA H2X, to 1998 Base model 29 Outlaw, to a Loaded 2002 29 Outlaw, and currently I'm looking for a 35 to 38 Fountain/Formula/Cig. Having a small fast boat makes a lot of sense until you get in 2-4ft. chop. I boat on a freshwater lake and it turns up in a blink of an eye. In boating nothing beats the length of a boat for a comfortable ride. Your family will Thank You. Reading your above and past thread would you ever consider a larger older boat, perhaps a 1990-1995. You may be able to get into something a bit larger for the same money. Sure you won't be the fastest thing on the lake but you'll have the nicest ride Just my .02 Good luck shopping.
Ough yeah, don't strap your self $$$ to buy a boat. It really takes the enjoyment out of a day on the water. Your alway stressed that somethings going to get scratched, banged, ripped, etc. etc.