Law Of Diminishing Returns?

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. 

Finding a "happy medium" is hard but worth the effort. The old saying to "never buy an entry level or top of the line" item is good advice. Be patient, enjoy the process and hopefully you'll achieve an end game audio system faster than many of us did.

I spent a lot in the past 2 years but the goal was my "End Game" system. My biggest purchase was my amp. I revamped my system in reverse. I bought speakers that will serve me well for a while , but still knowing they probably would not be my last.

I spent on my amp and am having a preamp built by the same manufacturer to compliment it. Those two pieces will definitely be end game.

At some point I will upgrade my speakers , the electronics ( amp & pre) will not be outclassed by a "better " speaker .

Another element of the audio journey which both OP and respondents have left out is the pleasure of the journey itself. As with travel, often the voyage is as important as the destination. With every equipment upgrade, and slow adoption of every new technology, I have found the process of adaptation and expansion just simply a Fun Activity. When upgrading components I focus on ONE at a time (including cables) so all other variables are kept constant. Is the $5k amp 2x better than the $2500 amp? Not even close. But is it noticeably better? Sure. I find the degree of improvement best tested by moving backward: once the ears have embraced the $5k amp, backshift to the $2500 amp now in your secondary system. The downgrade is more noticeable than the upgrade. And there is great enjoyment in Learning Experiences such as this one.

+1 for @russ69