I think there is a lot of difference in how people appreciate music; it seems in my experience there are two fundamental approaches: Reliving vs Remembering.
Yes, those are valuable distinctions. I believe I'm a synthesis; reliving the moments when I got some truck-load of speakers to actually cohere and play together, and so I tend to play the tracks I used to judge the system back then. Lots of Steely Dan.
There is of course another alternative POV, which says that the sound mixer/recording engineer listens to all of it through headphones while s/he is making the master; so why shouldn't we listen to it that way...?
If you mix an album on cans it's going to sound OK in cans and nowhere else. A decent pair of neutral monitors is a much better proposition. It of course pays to check the mix in cans, as well as on a boom box and perhaps in the car stereo.
On neutral monitors: I almost won a pair of Yamaha NS-1000 yesterday evening but they went beyond my pain threshold.
TE: Also a 3455A went past, much the same way. The seller of the 3455A is known to supply a steady stream of quality gear, so has many followers, and there's almost always a bid fight. The NS-1000 were sold by a church charity, who do a "too good" job of describing the product, and people find them.
I'm actually most irritated over missing the NS-1000. I really like that speaker. It is hated by many, and the 'phools don't like it, probably because it is so obviously a good piece of engineering work, high but not over-the-top quality furnishings and so on, but with things like the Beryllium membranes that in and of themselves would be pretty close to 'phool class, though. But here, they're in the construction for a good reason. In the end, it is extremely revealing: It will play the recording as it is. Obviously, people don't want that, they want "musical". Fuck that.