I don't have any recordings or experiences where I said, "huh, I really liked the way that sounded before I upgraded, but now with a higher resolution system it doesn't sound as good to me." I do find that as my system evolves and (hopefully) improves, I realize that there is music that I like that doesn't warrant sitting there "critically" listening on a high end rig. But, in these cases (for me anyway), it didn't warrant it on a lesser system either. I might have hoped that it would improve, that what didn't seem like a good recording might fare better on a better system, and it just didn't work out.
An experience I do have, regularly, is realizing that there is music that is not stellar in it's recording quality but that I like a lot, so I listen to it when I'm not critically listening, either up walking around, in my office, in my car.
Maybe I'm just justifying the continual improvement of my system, but I find that each improvement makes a good portion of my music sound better and be more enjoyable to listen to or neither betters or worsens it, but does not make anything less enjoyable than it was. -Kirk