I've been browsing thru Craigslist and other sites to start getting a feel for what's out there.
How far back do y'all think I can go back safely? Initially I was thinking of 2000s, but some of the boats back to the mid-90s look decent. Of course, I'm seeing the sharp drop in price as years go on. What would be a good year boat?
Tough to say with boats. Many are produced in small factories, and the built quality can vary greatly. The hull isn't as important as the motor, so a late model motor on an older hull would be the best. Of course, you should get better overall quality from one of the bigger boat builders.
Things to look for are wood/rotten stringers, transoms, etc. I would spend a good amount of time finding someone to check out anything you consider purchasing, someone in the know, that knows what to look for.
