Really interesting post/question.
I gotta say, I had an epiphany a while back and it really struck me: I realized that, when it comes to chasing tone, my mood has a huge impact on what I dig. Seems like a small factor, but IME, for me, it’s impact is massive.
I can play a rig and find it just blah, not “there” and so on. I can then come back to the same rig—same settings and everything—and totally dig it. Weird.
Or maybe not weird. If I’m feeling inspired, excited etc, I actually hear the rig differently, interact with it differently. What was recently blah is now the shit!! Noticing—and then getting my head around—this phenomenon has really changed my approach to chasing tone. For the better.
Epiphany number 2: whatever I’ve been playing recently has a huge impact on how I perceive and hear a new amp—or speaker or whatever. It’s like your ears become acclimated to a certain rig/tone, and whatever you play next kinda goes through that “filter” in your brain. IME this can really affect how you hear and perceive the new gear.
Those two things have totally changed how I approach chasing and assessing tone.
So, I try to be really sure before I sell something. And I especially focus on those two thangs.