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I think there are many issues at play.
In terms of cost/value... the vintage instruments are what they are and they are not making anymore (yes, there are reissues, but like reprints and other recreations, they are not considered the same). As such, a genuine '59 Gold Top will always be sought after and will command a premium price.
In terms of quality, while the myth of all hand made instruments and how everything was better in the old days persists, the fact is that these instruments were very much dependent on the hands that made them, and even when in very high quality hands, much of that skill was often used to compensate for issues in the quality of the specific wood, etc. Compared to modern production quality, I don't think the good old days were really as good as some think (I am still amazed when I think that PRS manufactures their wrap around tailpieces with no intonation adjustment as their manufacturing tolerances are so tight it's not needed; high claim, but also one I've found true on all the examples I've played)... but...
There are two considerations about those good old days. First, because there were so many more instruments all hand made, there were many more highly skilled workers putting these together. Even if not all were expert luthiers, the finished instruments were professionally setup to a better degree than you find in off the shelf instruments today. And then there is the wood!
Vintage instruments finished in nitrocellulose have been aging and improving all this time, and they have great tone. Add to this fact that Honduran mahogany is rarer and more costly now, or Brazillian rosewood is so severely limited now, and you have a better picture of desirability.
Still... on a high end modern guitar, you are often dealing with aged tonewoods, with modern manufacting tolerances, assembled and finished by highly skilled luthiers. It may lack the perceived "soul" of some vintage instruments... but,
My two favorite guitars that I play and record with most often are far from vintage: A Parker Fly and a Taylor T5. Both amazing instruments with fantastic tone (and alot more flexible in their tones than vintage instruments).
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