I would start in 1973, when I bought and built a Dynaco SCA-80Q at the desk in my dorm room at UW-Madison. My roommate and I each bought a pair of The Smaller Advent Loudspeaker from the "Happy Medium". We agreed to split the system. He bought a Dual 1215, probably with a Shure M91E.
I know that many of you might sneer at the Dynaco SS amp, but it was a learning experience. When we split up as roommates, I bought an AR XB, which I still have, albeit with a Grace 707 arm in its current incarnation.
I have arrived back at a pair of Smaller Advents paired with a Knight Kit KA-40 16Wx2 tube amp that my Dad originally built in 1959-60. It is my workshop stereo, enjoyed almost daily while I work. Mostly streaming now, from digital files on an iMac connected through an Apogee Duet. It is really enjoyable system! The Duet dates from my silly project of digitizing all my vinyl instead of listening to it. I stopped when the law of diminishing returns was applied.
My main system is Linn, 1983 LP12, Accurate Kontrol, AV5125, Active Keilidhs, Mac Mini, iFi Nano iOne. Both systems are enjoyable in their own way. I play around with Amarra, BitPerfect, Tidal, Spotify, Apple etc. but the above law applies to that as well. Started with LP12, Kans and Denon power amps in the 80-90s, then to Arcam electronics, then to Linn.
Not exactly an answer to OP's query, but I'm still enjoying authentic vintage gear that has withstood the test of time. Plus, my 95 year old Dad loves that I have his old gear and use it!