As most of the others have said, play a bunch of guitars and find the one you love. Even the most staunch Gibson fans will tell you that you may have to play 20 new (or vintage) Gibsons (same model, options, etc.) before you find the one that stands out.
My one Gibson I have is a 1936 L-00 (I guess you'd call that vintage...

), and when I bought it, it was only because it sounded unbelievable, and played very well, too.
Somebody in the thread said that you'll pay the same for a vintage guitar regardless of the condition. That's really not true. My guitar was $1400 - it doesn't have original tuners or an original bridge, and the shop I bought it from basically restored the thing from some water damage that had caused some of the glue to loosen. I didn't care about any of this, because the luthier does amazing work, and the guitar sounds as good or better than any other acoustic I've played - it made me appreciate what it means for a guitar to be "alive." (It does have a unique sound, which is perfect for blues, etc. It doesn't sound like a Martin, but that's cool.) When I asked others about it (Gibson guys lol), they said that the guitar was worth it based on the sound and my love for it alone - and the fact that it won't really depreciate.
If this guitar was in great, original condition, it would go for $2000 or more. The shop I bought it at is awesome, because they get great old guitars that are players - they often aren't original, etc., so because of that they are more affordable, and are still killer guitars.
I never believed there was anything "magical" about vintage guitars, and I guess I still don't. There IS something magical about this one though...

Play a ton of them and find the one that calls you.