Interesting post. Thinking about my own Gear Journey, I’ve only bought two components new- a turntable to go with the used Fisher integrated bought in 1970, and a Hsu subwoofer bought in the mid 2000s. My systems have improved incrementally over time and IMO always punched above their weight in terms of cost. New purchases followed an increase in listening skills, discernment, knowledge of acoustics, and opportunity (finding a pair of JBL 4430s in a pawn shop, for instance).
Am close to the end of my gear journey now, listening to speakers I couldn’t even think about buying new and a lightly-used, great sounding preamp. Total between the two last year was just under $12k. That is magnitudes more than I’ve spent on my stereo at one time … ever.
Agreed on the 80/20 rule and think the cost-quality curve is exponential. There’s probably better sound out there. But I get stuck listening to music for hours now. I’d rather listen to music than watch TV or movies.