This thread definitely goes to the heart of the matter- more than anything, for so many of us, the pursuit of HiFi happiness is a sentimental journey.
Mine began when I earned enough money singing in a boys choir to buy a used Yamaha CR820, Ohm E bookshelf speakers and an odd-looking belt-drive turntable with an orange felt slipmat. I then learned to solder and built a board to control a small portable lightshow, and dj'd for friends' house parties, upgrading the audio as I made more money with that (SAE II preamp, Sherwood 100W Mosfet power amp). Meanwhile, I cruised Montreal audio emporia, intrigued by the cool-looking Naim and Quad gear, and sort of put off by the odd gothic MacIntosh aesthetic. At that time, though, I wasn't really looking for sonic delicacy- it was more important for sound to be clean and loud. That peaked after college when I had pro audio bass bins and horn mid/tweeter arrays hanging from chains form the ceiling of my loft in downtown Boston- still had the SAE and Sherwood at that time, but paired with a Dual 704. Moving West I ditched the big speakers and the PSB bookshelf speakers for the bedroom but kept the amps and the turntable, and a pair of the cheapest Yamaha speakers that were surprisingly good until after grad school, when I started chasing the hifi dragon again, getting a pair of Klipsch Heresy II's. Soon the solid state amps went downstairs to the studio to go with Yamaha NS10's for sound editing, and a Scott 299C came in the door for the Heresy's, and the Dual was replaced with an AR the Turntable. This is when upgrade fever started to take hold. AR parts got swapped out for new suspension, armboard and a Rega tonearm. It became clear the Heresy's are very limited speakers, sounding really good with only a very small range of music. I went for Cornwalls with Crites crossovers, selling the Scott and getting an Eico HF81, which I had rebuilt, adding a custom african hardwood faceplate (it was a console pull). While definitely an upgrade overall, I couldn't tame the bloated mid-bass, sold them, and got serious with a pair of One-Thing Audio rebuilt Quad ESL 57's. Back to the future! Mid-to-low volume delicacy now being primary, the slope got seriously slippery from there on out. Now I've got multiple systems of mostly vintage stuff in the various places where I spend my time. All in good fun- the systems are the best anti-anxiety treatment out there!