I feel your pain. Haha. I'm 25 and just got my first boat. I guess the most important thing I've learned is don't let people call you crazy. If you really want this (and you have to know that) then do what it takes to make it happen. I searched high and low and eventually jumped on a really good deal I found on craigs list. And by really good deal I mean a well used but solid old boat that needs some work (the phrase "keel bolt replacement" is lurking in the back of my mind) for not that much cash. I guess what I'm being long winded about saying is, if you can afford the time and effort and hours, get the best thing you can afford and be prepared to throw some dollars and mostly sweat equity in it.
Or, you and the missus save up, and get somthing that requires a bit less attention other than regular maintenece. Do obsessive resarch...
'70 Columbia C26 Mk II - "Klydo"