I'm suprised at all of the positive feedback

I was expecting the "you're insane, get a life" responses more than anything. Very cool to see there are some people on here that have done this themselves.
Honestly, if I were buying the boat outright I would be looking to spend less than 50k on it. I'm not baller status yet, and I make my income off the size of my trading account!
I've done overnighters and stuff on a 19' starwind for a couple days so I think a 40' would be like a damn palace to me. Sounds like a 35-40 footer could do it.
I've never really been seriously into sailboats (against my fathers will). Are there any specific boats out there to stay away from? Bad manufactures? Some of the older boats i've found (late 50's-early 60's) have wood hulls and a lot of teak. I'm thinking that would only multiply the maint. expenses. Trying to stay with a fiberglass hull if i can. Are there any good boats in that price range you would recommend? I don't really care about the age of it, so much as its quality and in good condition.
Also - are there better places to look for boats at cheaper prices than others? I.e. not looking in newport beach/san diego, but rather up the coast a bit or inland?