Re: *Thinking* about a bigger, better boat
I went from a 1966 Pearson Triton (28 ft) to an '86 Catalina 34 this past fall. While I haven't had a chance to sail on the C34 yet the room down below is really impressive. I've seen ads for C34's that are older than 10 years, but are very well taken care of. And you can get them for a lot less than $100K. C36's too.
The first C34's (like mine) had deck stepped masts, then they made keel stepped masts an option (I think in '87) and a lot of the ones I've seen are keel stepped. Then at some point I think they went back to all deck stepped masts. You could still probably get one of those later ones for under $100K.