Happen to you? Gear chasing because the fundamentals were wrong.

If I had to do it all over again past 45yrs in audio gear chasing, I would have started by stepping up a little more $ on higher quality and better matched sources and amplification [sooner]. Building my own speakers since the beginning, a few nicer source-players and amps along the way sure would have helped me to realize a few key things around sound and music much sooner. Once i did, my own speakers started to sing for the 1st time in a very nice way. Lesson learned late.

An old buddy pulled me in to listen to his new source and new tube amps once, it was game over. Learning from others who cycle gear and take detailed notes is helpful to get going in a better direction, sooner. The OP knows this too. :) 

I'm newer to this than most of you, but chasing wattage and not understand speaker sensitivity were the two biggest for me at first. Once I got that out of the way, the next revelation for me recently is the quality of DAC. A/B testing was a bit shocking. When I do upgrade, I could see myself stretching more for one than I would on an amp.

For me it is and always seems to be amp-speaker synergy and noise in the phono playback. I am learning a lot on this forum and it has helped tremendously! It seems when you match equipment it is so much easier. I purchased a decent phono stage finally with its matching power supply and it transformed my turntable/ cartridge playback (no noise) simply amazing. I now keep my amp and preamp choices to the same brand and it is getting better for me. I never had a problem with wattage because I never could afford a powerful amplifier. Now I have seen how efficient well made and designed speakers can play with much less wattage. I will say for a big set of speakers that are not Klipsch more power is pretty amazing in sound. The bass comes out and is powerful and no sub needed. So tight and great sounding. 

Apropos hearing loss, mine is age-related, not due to damage. I don’t go much beyond 12khz, which is normal for a male approaching 70 years. This does not affect my hearing or judgement of the midrange, which is where most of the critical musical information resides. I’d say my judgement of what sounds "real" to me is as good as ever. Maybe I’m missing some high frequency harmonics on cymbals or whatever, but it doesn’t detract from my enjoyment. The system is tuned to my taste based on all the factors I mentioned, including tube choice. Switching out a rectifier tube can make a difference. I can still hear little differences in tone. The system is not "analytical" or "bright" sounding- to the contrary, it is a little on the warm side without sounding euphonic (to these ears).

PS: where I have difficulty is in public environments, like a noisy restaurant with high ambient noise- where I can't even hear a dinner companion to hold a normal discussion. This has little bearing on the hi-fi, where the ambient noise of the room is relatively low.