Cool thread; without going into all the minute details as Rob is saying, main steps for me would be:
Started playing music at an early age on classical piano actually; I think I've always carried this influence/experience with me in some way.
When I actually started the guitar, "good practice" at the time was to begin with classical / acoustic guitar; did so taking lessons for about a couple of years with a great Jazz oriented teacher. My only "gear" at this time was a nice Spanish classical guitar.
I Learnt the art of choosing the type of strings and ways to polish my finger nails to get the "sound" I wanted lol.
Joke aside, this was great education; still have a soft spot for great players who can mesmerize an audience and shine with an acoustic guitar alone.
When I was finally able to "promote" to electric, got a Gibson SG Std. I put all my saved money into it. That the guitar I really played the most all over my teens years, learning the "art and science" of the instrument, playing and tweaking it trying to sound like/emulate my influences.
My roots have always been in the classic rock / hard rock genre, and I've always been more into "vintage" classic kind of gear.
My first amp I got along that SG was a home made tube head + cab my father made for me, based on Fender Bassman / early Marshall JTM schematics. Another great education to have early on, learning how a great tube amp influences the way you play, the kind of dynamics available under your fingers, and how that is an essential part of the "sound".
All that early age also gave me the baseline for the "tech" part of the electric guitar, knowing how gear works and what you can do to make it your own & maintain it.
From there, I started in my late teens to very regularly research old vintage amps & guitars, trying to find the best sounding / feeling ones to me. Again, at first influenced by the gear my "guitar heroes" were playing, which then led to learning what I like.
Old 60's / 70's amps really are where my heart has been ever since; especially Marshall, Vox & Hiwatt. Few Laney and Fender here and there.
The feel especially, the dynamics, that go with the simplicity of those old designs and material used at the time, just can't really be replicated in more modern/complex amps IMHO.
I had been "guitar & amp only" mostly for almost a good 5-10 years I'd say, thinking "simpler/more pure is better".
I played old 60's stock Marshall stacks in bands at the time, loud.
After that, I started to experiment with more "effects" in front of the amps.
At first mainly to push the amps more; fell in love with old Fuzz and Treble Boosters, and all kind of classic boost/OD pedals.
Then, to also "add color and texture"; went deep into all kind of old delay devices.
Btw another field where old classic simple amps shine IMHO, in the way they take almost anything in front and that you can use that to "sculpt" your own preferred unique sound/feel in the very minute details.
Finally felt the need to bring back some of my early age influences, tied to old keys / synths, and more "orchestrated" pieces & soundtracks / scores.
I added studio-like effect devices around my old amps & pedals, to be able to add "texture and ambiance" to parts when needed.
Mixing the raw energy / feel of old classic amps with more complex effects is where I've been ever since.
Amps can be old original "vintage" pieces, or some classic "hot-rodded" versions of those.
Oh, and during all those years of going deep into the "gear" rabbit hole to find the sound & feel I like, one key learning has been: speakers and cabs are essential.
"Tone and feel follow the speakers & cabs" could be a good catching summary.