In 1978, I started upgrading from a Lafayette LA-44 quad integrated amplifier and Radio Shack spacers that had served me in the dorm and my first apartments. My first high-end purchase was a pair of Phase Linear (Andromeda) Phase III speakers from Bob Carver and friends. I bought them in 1978 as they were being cleared out of a stereo store in a furniture store in Houston, TX. Retail was about $1695 and I think I paid about $1,200 on closeout. They are still in use as one of five systems around my house all integrated together via a iTunes/Apple Express router whole house system controlled by iPhones and iPads. This system is all classic… Denon DL-62L turntable, Koetsu Redwood Signature cartridge, Bob's Devices SUT, Carver C-1 preamp, and Carver M1.5T amplifier.

https://www.dropbox.com/sc/muhtua9be...bB6ZIDg2lH7F0a

1961 with a Thorens TD-124 TT, a Kenwood integrated receiver, and a pair of AKG headphones. As a teenager using paper route money, speakers had to wait until later.

We are not counting receivers are we?

C39 Preamp controller :)

Shortly thereafter added the 72770 amp

While the Kenwood receiver may not have been "high-end" it was all tube, included a phono stage, a headphone jack, and did a very credible job of passing the music from the Thorens table, still considered a classic that commands a handsome price, to the AKG phones. This combo provided a musical Epiphany that opened my mind to the world of classical music and fine audio.

1990's - DCM Timewindow 7's

The first system I purchased:

1) Technics SU-8077 integrated amp
2) Dual CS 606 TT
3) RTR 300D speakers

I'm still using the TT (with a better cartridge) and speakers. The amp is sitting in it's box in a closet.

Not that "old" in the scheme of things but a defining event was a pair of KEF R104.2 speakers complete with "Kube" adapter in 1990,
They led me through Sony ES gear, Rotel amps and CD players, Arcam transport/DAC combo etc, only retired 4 years ago as they really needed an expensive rebuild, driver surrounds, dried out tweeters, possibly crossover caps too, still covered up and stored safely waiting for "one day I'll fix them up" ....

Quad 2 preamp, one Quad power amp, one Quad ESL57 electrostatic speaker.

Not sure if this qualifies, but it sure started me on my journey. It was a Yamaha DSP-3090 AC-3 7.1 A/V receiver.

Garrard 301 turntable, Shure cart, Leak Varislope pre, Leak Stereo 20 power amp and Wharfedale Teesdale speakers.