Critical thinking and analytical thinking are being conflated here. I like the analogy to critical thinking, this should be a stimulating, intense exercise. Lets think about a critique, a critique doesn't have to be judgemental, it can be simple appreciation. That's how I listen during my relatively long listening sessions, I'm simply appreciating both the performance of musicians and the qualities of sound from both the recording and my system.
Now analysis is when one enters the judgemental mode. we are intentionally analyzing both the performance and sound quality, Analysis is inherently comparative as we need to have some reference for this analysis. This is the mode of listening which finds fault, cognitive dissonance and unhappiness easily arise here.
As for listening for sheer musical enjoyment, I only go here with far lesser audio systems where I need to avoid listening to sound quality since it would only cause unhappiness.
I too don't understand this seemingly increasing dismissiveness or negative connotations towards the critical. To engage in critical thinking or listening should be a highly stimulating, enjoyable, consciousness and curiosity raising activity.