Is Upgrading Degrading?

As your system and perhaps your ear, improves, I think you becom less tolerant of modern compressed recordings. That seems to be all you get in mainstream pop recordings these days.
Part of this hobby is spreading out your musical interests. As Kurk Tank says, meeting friends with a common interest, listening to new music at shows, picking up tips from the hifi press, all lead you into new areas. Currently, having discovered the ECM label, wonderful recordings and music, I am trying to find all I can

All things are relative in regard to the "high end". Just as long is to short, and shallow is to deep. In this arena we have no measuring sticks, consequently no one knows how tall or how short their system is in comparison to the next system, and brand names alone won't cut it.

I once met an audiophile at a repair shop who invited me to check out his rig. I was dazzled by the equipment, it looked like an add out of Stereophile. He was grinning like a "Cheshire cat" when I walked in. The expression on my face told him I was impressed.

After he turned it on, I was wandering what was wrong; it sounded like a good "mid fi" rig, but nowhere near what those names were capable of producing. Since I was in transit, I didn't have the time to either tell him something was wrong or help to get it right.

Names don't guarantee the sound even when they are new. We no longer have the high end emporiums that you could visit and make a "relativity check"; consequently, who knows what's short and what's tall.

Orpheus10, you clearly do. And so does everybody else. Your ears don't lie. The goal is reality. If you're hearing more resolution, you're hearing less distortion. It's really that simple. Adding "flavor" is simply adding distortion. Having your cake and eat it too means resolution that mimics reality. You can't have one without the other. The absolute standard is fooling your ears. IMO