I've had a bunch of old Gibsons and several newer ones. Many great choices but in my experience old guitars sound different than the same new model. Wood and finish ages. I have never, ever played a new model of any guitar, any make or model that sounded quite like its vintage counterpart. My main flattops the past 10+ years have been a 2003 AJRI and two early '50s Gibsons.
Don't get me wrong: there are good and bad examples of any guitar, any vintage. But if you're interested in old ones I'd say take your time, take a lot of time, play a bunch & learn about 'em and go from there. If you are interested in newer models, try to do the same.
Mainly, take your time to learn.