Wonderful dialog! It makes me dig a bit deeper and realize that the two dimensions of "listening to music" and "listening to reproduction" can easily co-exist.
Think about all the dimensions you are absorbing in a live performance. The musicians interacting with one another and the audience, watching the musicians play the tools of their trade, listening to the acoustics of the environment and listening to the music itself. At home, there is the music, the environment and the reproduction. I take delight in noticing how well the sax or bass drum sounds. And I take delight in the music. Everything works together for me. Noticing the capabilities of my system goes hand in hand with enjoying the music itself, just as noticing the character of the musicians in a live performance goes hand in hand with the music. Critical listening goes beyond the appreciation of musical reproducion and is the focus on the reproduction for purposes of diagnosing a system.
In the most negative sense, critical listening can also be noticing the worst aspects of your system whenever you listen -- hopefully, that doesn't happen much. If it does, it's time to change the system, change your priorities or change your drink ;-) Great discussion all!