My 81-yr old mother & all her friends (in their sixties, seventies & eighties) say that the best sound (after old (tube) console record player/radios) came from the old Sony Walkman players. They use words like "warm" & "full". They all pretty much dislike CDs. Maybe this has to do with hyperacusis or other hearing changes that occur with age.
They also generally dislike newer TVs, and prefer the sound of VHS tapes over the sound of DVDs.
Funny thing is, I tend to agree with them. I can tell that their preferences are lower-fidelity, but I often just *like* the sound. I find it easier to get caught up in the emotion of recorded music when it's slightly distorted somehow. Although true, natural, symphony hall reality is better than any recording, of course.
I have a theory that distortion is the sound of emotion and we all pick up on it at least subconsciously. The voice of someone expressing emotion will distort compared to when there is less emotion. People push their musical instruments (including acoustic instruments) to the edge of distortion as well when playing emotionally. As an engineer I think it's a cop-out to try to fake emotion by adding distortion (aural exciter, anyone? or cheap tube gear to "warm up digital sounds"?), but it can be effective in very small doses. (HEDD?)
Even a low-fi visual (polaroid, super-8, VHS) can trigger a response that a higher-resolution version may not. They can look more like how our memories look to us, if that makes any sense.
Okay, now I'm rambling...