The gear most of you use is not what normal consumers use. The quality of that has been deteriorating, both in terms of source and reproduction equipment, for about the last 30 years.
Why would reproduction equipment have been deteriorating ? Even a cheap DAC on a portable player or similar device can be better now than expensive "hifi" analog sources were for playing cassettes or LPs a couple decades ago. The typical quality of the production of popular music has been getting worse, mainly because of the loudness war, but that is a separate issue. There is no longer a real technical reason for high quality audio playback equipment (other than transducers) for listening with dynamic headphones, or speakers at a power output suitable for home use, to be expensive with large scale production.
I am usually quite careful to state any assumptions or obvious exclusions and so I did say that the advent of better technology in Turntables (materials mostly, and smaller more efficient motors and transformers) and DACs and Headphones and no doubt some other areas has finally started to reverse this trend.
Cassettes could be thought of, quite validly, as the first consumer compressed format, it was just analogue compression, which, to put it mildly, is pretty crap. Cassettes were always a dreadful format and only became popular in the Western Economies because LPs were so expensive. In the 1970s, when music was a much bigger part of culture, and particularly youth culture, than it is today, we all used to record each others stuff onto 'green meanies' the awful BASF C90 Cassettes.
Some people with 'short arms and deep pockets' only ever copied other peoples records and never bought any. They went on to become great leaders in the business world.
But almost everyone stopped using them after about 5 years, once they realised that anything played more than a handful of times and/or more than 3 years old, now sounded awful - whatever cassette brand you had used. Better brands just slowed their inevitable decay.
And then along came the Sony Walkman which gave them a whole new lease of life, because of the convenience and freedom factor, which is more important than sound quality.
Those of us who cared about the sound, just had a mental list of the stuff we liked but only had on cassette and gradually picked some (but not all, as I have been having so much fun discovering) of those LPs up as we spent our Saturday afternoons browsing through second hand record shops. But we were in a very small minority of people worldwide.
The really interesting thing about Cassettes, which surprised me, is that they were the biggest selling format (pre-recorded) worldwide between 1982 and 1993. There is a really nice graph which shows this here. Just scroll down to the third graph and it shows this brilliantly.
http://www.stopmusictheft.com/music-sales-analysis
Before CDs really started to catch on in the 90s, vinyl had already been replaced by cassettes in the 'bulk consumer market' and so clearly convenience and freedom were far more important to most people, and particularly in poorer countries and communities, than sound quality was.
So before anyone says, 'Thanks for the history lesson but that is off topic'.
No it isn't.
It is the same situation you are discussing here except that MP3s are a lot better than Cassettes.
The opinions of any of us on here, myself, Greenears, Rrob, Bigshot, stv04 have no bearing on what the main consumer market will actually do, because that market cares about convenience, then price, then a tiny bit about quality. It is still an interesting discussion though :>)
A typical vinyl HiFi setup from say 1984 owned by someone like me in their mid twenties with a half reasonable job and an interest in music (but not a HiFi obsessive) would sound far better than a cheapish DAP from a couple of years ago playing 16/44 files. Everything else being equal, and using high quality recordings, which is very difficult to achieve and I am not suggesting you try.
It may or may not sound better than a top end modern DAP playing well recorded and mastered 24/192 files. Though I wouldn't be at all surprised if the 1984 vinyl setup up lost that competition.
You haven't quite got my point about deterioration in quality because you are probably a lot younger than me and don't remember all this.
It started with Vinyl pressing quality. It started to deteriorate in about 1973 and within 5 years the QC had gone completely.
Many more steps followed along the way in many areas, There were of course some improvements as well, but the general trend was always downwards.
Compression of loud music on CDs and Radio is just one of the more recent events, in a long chain of many events, which all have one thing in common. A reduction in quality at another point in the Audio chain.
I really do hope, and indeed believe, that has now stopped and is going to go rapidly into reverse over the next few years, and those of us with the time and the money will get the quality that we used to take for granted. In fact maybe considerably better quality than that. But it has taken a long time.