Vintage

I'm starting to look at older, calssic instruments. I'm just looking for a little advice on what direction to head. I'm not really that impressed with "reissue" stuff. It's still new, and I don't care what the manufacturer's specs were back in the day, I don't believe that the quality is as intended. I mean, what's the difference, really, between a 2010 American Strat and a '69 reissue? Of course, I don't have $20K to drop on a guitar either. $2K is my max...now, what should I be looking for, age wise? I'd really like a Fender Strat. A nice Les Paul is also under consideration. Just one at a time. I don't know a whole lot about the specific construction details from year to year, so besides some buying advice, I'd like a little education out of this shopping experience. Thanks in advance.