What's the most fun is the radical, advanced jazz players - who insist that not only is rock and roll primitive, backwards music, but that their guitars should sound like 50's throwbacks. Or throwback toodler Wynton Marsalis, insisting that Miles David "sold out" because he didn't keep sounding the same as he did when Wynton Marsalis was growing up.
I do like to keep at least one guitar strung up with something like 11-52's with a wound third string - every once in a while, it's nice to play in tune - and flatwounds make for fine slide playing. But once you start fretting on them, they go dead pretty quick even to my ear. The whole system that's evolved together - strings that sound good through the average amp sound, amps designed to sound good for the largest average types of guitars, guitars that are built to make average pickups work best - "average" in the sense of "in-between", not average meaning bad - you can't get too far off the center point before you can't get back to normal.
Context is important too - what sound great by yourself in the living room may be just a dull thud in a band, especially if everyone's trying to "cut through the mix", one of the all-time worst ideas available. WHO'S IN THE MIX.... And I'm pretty sure you can't take the word of any guitar player who started playing full-time professionally in the 1960's, even the mid-to-late 70's. All these guys who insist that the in-ear monitors have "solved" their deafness problems - hey, Keith Richards and Eric Clapton and Pete Townsend and John McLaughlin ain't hearing what I'm hearing, that's for sure. :-\
