This would be a good place for the meme that has a picture of Jimi playing at Woodstock and says “Jimi Hendrix seemed to enjoy himself at Woodstock despite the fact that is pedals were not true bypass.”
It's a great question. In my experience, chasing a particular tone never seems to perfectly happen. I basically gave up on guitar for awhile because I felt like I was always chasing tone.
This time around, I'm happier with maybe just a general idea in mind, but essentially getting the gear I like and having the tone develop. I got the guitar I wanted, then played that model guitar through different amps and chose the tone I liked, then did the same with a pedal or two. I have 2 pedals I bought with some expectation of tone and am disappointed in both - great pedals, but they subtract from my rig instead of add to it.
Last night I was playing my 594 SH (double cut) into my Sweet 16, fairly cranked. No pedals (very unusual for me). Doing (well trying to do) some finger-picking David Grissom style on a song I wrote a couple of years ago. Then I just messed around with some other stuff, still finger picking (also unusual for me), an basically noodled for an hour or more.
I was in tone heaven. It was exactly the tone I wanted at the time.
Tonight, if I want to play some Gilmour-esque stuff, I will need to take a different approach (strat style guitar using pedals, for example, into a different amp perhaps, and definitely using a pick!) to dial in the tone I would desire in that case. There would be no point in starting with the 594 straight into the Sweet 16.
I think that is a big part of chasing tone - your target is often moving, so you need to anticipate that, and intercept rather than chase.