It really does depend on the guitar, even within the same make and model. For instance, Tacoma is making some great Guild guitars right now that are right there with the 60's Hoboken-era Guilds, and are priced around the same as the ones on the used market, so it's a real tossup which to pick.
On the other hand, a Brazilian Pre-War Martin D-28, if structurally sound and set up right, will blow the barn doors off a modern HD-28. But then it's like 25 thousand dollars more, so it better!
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