Mark,
It sounds like you're in about the same boat as me, so I'll chime in. I am 24 yrs old, have a wife and baby, and have a very small aviation budget. I am VERY fortunate to have a dad who financed my CFI rating and also my Kitfox 2 which I keep in my garage and tow with a towbar. At the risk of being shunned, I will confess that my dream airplane is actually a Bearhawk because it can haul a family and baggage, and I can SCRATCH BUILD, which means I can spend a couple hundred bucks on enough aluminum to keep me busy for 6 months, and that leaves me just enough money to top off the gas tank in the Kitfox. When the Bearhawk nears completion (in about 5 years) I hope to sell the kitfox to pay for some used avionics and FWF. So that is my method of keeping me in the cockpit until my dream plane takes form.
I'm not aware of any scratch built airplanes that are as fun as the kitfox, but there's something to be said for their affordability over their kit-built brethern.
Oh, and I am also VERY fortunate to have a wife who not only tolerates my madness, but has actually deburred more aluminum parts than I have!
Nick