Nice post dude.When it comes to guitar tones I tend to prefer the old school approach of an amp of choice, a few pedals and proximity to speakers for feedback effects. It seems that all the OGs of prog did some combination of this sort of thing to achieve their sound. No one really sounded like Fripp or Gilmour or Page because their set-up and technique for using it was all their own. Someone might try to imitate it but instead of doing it picture-perfect would develop a similar sound yet one all their own through trial and error. The digital effects era now offers at least hundreds of effects at the touch of a button or is a mouse-click away. The Internet lets you communicate with other musicians or music fans and find out what a particular guitarists rig is and what his settings are -- suddenly you can at least have a tone that's just like that one. Rather than create infinite diversity in infinite combinations, the technology has made it possible to have dozens and dozens of sound-alike guitarists who are simply adopting a tone because they like it from hearing it.
I also think that the popularity and influence of the guitar institutes and schools has forced an orthodoxy on playing styles especially when it comes to virtuosity. Is there some rule that I don't know of that says one must revere Joe Satriani above all other guitarists? I may like some of the trickery of this kind of player but no matter their virtuosity they will never approach (in my mind and taste) the uniqueness of a Holdsworth who, for lack of a better word, was and is a freak of nature. His natural gifts or quirks give his shredding a fluid feel that seems lacking in the metal era approximation. As for Holdsworth and tone, his guitar solo during the Soft Machine song "Hazard Profile" doesn't buzz or crackle or crunch, it just takes that simple tone he's using for his guitar and then wows you with those insanely technical runs.
This is my take on guitar and is all from the point of view of a music listener and amateur musicologist (and overthinker).
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