I'd also love to hear all of your thoughts on the matter to
I was brought up in a home full of music, mainly piano and singing. I made my own recordings on a mono valve tape recorder as a teenager and played LPs I'd bought on my Mother's radiogram but didn't even know HiFi existed until I left home to do an engineering apprenticeship.
I discovered it when I wanted something to play my LPs on.
I ordered a record deck recommended to me at my local music shop but when it came it had no cabinet and no cartridge. I had not expected this, so I decided to learn a bit about it.
I made a plinth for the record player and got a ceramic cartridge which, wired in mono, was an acceptable match for the microphone input of my tape recorder, which I could therefore play records through.
I built a fair few bits of kit in the early days when I had no money. Headphones weren't a thing at all really then, and I still only use them if speakers aren't available. There was no subjective audio fashion at all back then - all engineering and measuring it worked properly.
It was years before there was a portable music system and when the first Sony Walkman came out I saved up for one (it was very expensive in real money back then).
Anyway, I got busier and richer and ended up more easily being able to afford good reputable stuff to a greater extent than time to properly evaluate it. Subjective audio was in full fashion, as it still is - a lot cheaper than needing expensive measuring equipment and requiring zero technical education or knowledge, so it proliferated.
I ended up with some nice stuff and continued to enjoy music of many sorts as my main leisure activity.
LPs changed to CDs but I kept them, and the record players I had accumulated.
When I retired I decided to upgrade my DAC to one which had the ability to decode a wider range of different file types and, having lots of time, decided to evaluate them properly myself.
I compared models from very expensive to what I thought then was cheap (£1000) and found to my amazement that when I matched the levels accurately and got my daughter to swap between them the differences in sound which I was sure I heard really weren't there. I repeated this quite a bit since it went against what all the magazines said but no, whilst I could hear the differences some of the reconstruction filters made all the DACs were so close at matched levels I couldn't hear a difference enough to be sure which I was listening to.
This was a surprise to me.
Anyway, I am not deaf, I still hear differences between microphones, record players and speakers (and headphones) but not DACs.
I am also pretty sure as long as an amp has enough power (not all do) they sound so close to the same to be of no consequence too.
A powerful enough amp is still not cheap but DAC choice is all about functions, reliability, styling and so forth, not sound so if it has the facitities you need it can be the cheapest part of the system!
So after 52 years a hifi enthusiast, user, home builder and engineer I have come full circle from owning a DAC the price of a car to being content that the internal DAC in an integrated amplifier is indistinguishable from such an extravagance on music recordings.
I do have quite a few headphones but mainly for interest's sake, for enjoyment it is speakers, many hours per day.