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I've spent a little while really thinking about this discussion and i'm glad. It's made me really think hard about what it is I actually want. As it happens it's not a vintage guitar. I do like the idea that an old vintage guitar has been around and has history but as has been said, it's a risk and there are some modern guitars that are easily as good.
I have come to the conclusion that Mojo comes from within and as has also been said (Somewhere), the best guitar in the world is the one that you fell in love with.
If I wanted a top notch guitar I'd bit a modern one.
I agree that older acoustics 'play in' over time but the standard of construction of a modern Martin, Santa Cruz, Collings, Taylor, etc is beyond reproach.
I can see no reason why a well played 'newbie' wouldn't develop into a guitar that would rival one from any era.
Studio: https://www.voltperoctave.com
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"Take these three items, some WD-40, a vise grip, and a roll of duct tape. Any man worth his salt can fix almost any problem with this stuff alone." - Walt Kowalski
"Only two things are infinite - the universe, and human stupidity. And I'm not sure about the universe." - Albert Einstein
I think for some there will always be guitars you aspire to own because of other factors. I'll always aspire to owning a black les paul custom and a guild S100 because some of my favourite music was made on them and they look cool as fuck. Im not bothered about vintage though.
A few years ago I was searching for a '75 hardtail strat (yob and bit of billy corgan influence). I was very disappointed with the ones I tried so gave up. At the time they were seen as a poor example of fenders history and subsequently were only about £450. Now they're going for £1500+ because they're a bit older. For half of that you can by a billy corgan signature, which is a significantly better playing and sounding guitar.
Kelvin
With Strats it was often because design improvements (the Micro-tilt 3 bolt neck joint being the most obvious example) were badly executed. Manufacturing tolerances were poor, neck pockets were over-sized and the join was unstable.
It was exactly these kind of things which resulted in the 'Older is better' belief among players. And at the time, it was true. Incidentally, a Strat came in four variants; with or without trem, 1 piece maple neck/maple neck with rosewood fingerboard. Colours choices were extremely limited too. The Dan Smith/Bill Schultz era signalled Fender attempting to remain their lost reputation.
Now they make endless variations, across an incredibly wide range of price points. Even the cheapest are pretty good.
Subsequently, makers like Anderson & PRS has redefined what quality looks like and have caused other companies to up their game.
A modern guitar may not always be made from the finest tone woods but it is likely to be better made, better value and more playable 'out of the box' than instruments from any other era.
It smells bad. Beyond that, I wasn't interested because it had a fairly big chip in the finish at the bottom. Yup, it was genuine wear and looked old, but that doesn't mean it looks nice...
Although, with drastic work they can actually be quite nice - but this shows the stupidity of the vintage market because with a refinish, neck pocket repair, re-contour and new bridge, you "destroy" its "originality" and hence "value". I did that to a boat anchor of a '79 one once, it made it a nice guitar... and about a couple of pounds lighter!
But I've also played a complete dog of a '57 that, even though also refinished and with a badly-done neck shave, was still "worth" much more because "it's a '57 Strat".
ie age trumps originality which trumps being any good as a musical instrument...
Which still doesn't mean that the very best as a musical instrument might not be an all-original 50s Fender or Gibson, it's just that the reverse is not necessarily true.
"Take these three items, some WD-40, a vise grip, and a roll of duct tape. Any man worth his salt can fix almost any problem with this stuff alone." - Walt Kowalski
"Only two things are infinite - the universe, and human stupidity. And I'm not sure about the universe." - Albert Einstein