Ok, here is my first attempt which is focussing on gear.
In my case it is so that I have a few vintage amps and preamps. Over the last 30 years they have all been used for a longer period of time. I never switched gesr for reasons of new fashion. Four Quad II, two Leak Stereo 20 and in the meantime a 1994 Audion 300B. Preamps were the old quad tubes and a very simple Croft, which I like very much. It has no voltage amplification, only a cathode follower. It works great with the Leak Stereo 20 because they actually have the last stage of a preamplifier as the first gain input. I collected these treasures and never sold them.
But since the last 18 years a system has been established which I listen to everyday. With all pros and cons I am very satisfied with it. A CE22 commemorative edition from 1996 and a MC 275 MK4 from 2003 or 2004. I like the sound even if they have transistor gear in the power supply unit.
With loudspeakers I have never been the exchanger to want any nuances of marketing. I was interested in the principles of sound conversion. When I was 15 years old, I built the first horn systems together with a friend who was three years older and had a very good command of mathematics. Full horn, also in the bass. When I was 19 years old, I built a Klipsch corner horn. Unfortunately only from chipboard but it sounded quite good.
Later I replaced the midrange and tweeter horns with a 10 inch Tannoy HPD, together with the Klipsch Eckhorn I built myself. I would love to hear this system again today...but it has been scattered to the winds for decades.
I never traded my devices quickly but always listened to them for a few or many years. My best transistor sound when I was young was a used Quad System 405 with 33 preamps. They fed HPD 10 inch Alnico Tannoys in my dorm room. There was no room for horns. In the 90s I bought two pairs of used ESL57 in London.
I had the ESL in a frame two above each other. That was very cool. It was followed for many years by BBC monitors, then a Tannoy Canterbury. From 2008 to 2018 I had Klipsch Jubilee in my living room, the only one in Germany. It wasn't my wife who wanted more light in the living room. It was actually me. But in addition, after 10 years of full horn two-way system, the desire for a more intimate sound reappeared. Even though the Jubilees were already very good with TAD 4002 drivers. Just...there was a DSP involved and that bothered me more and more. In the end I had them passive, but that didn't work so well with the TAD (or I had to build a new Xover from scratch) and the other drivers for passive were not so good. But this speakers are still in my office.
So since then I have a BBC loudspeaker again, a Stirling Broadcast LS 3/6. These speakers are very close to the old kitchen radio. Turntable is an Oracle Delphy with SME V, very nice.