I listen to my system in different ways depending on the source, the time of day, what else I might be doing at the time and what mood I'm in.

My system is in use for most of my waking time when I'm at home, and is used with different sources for different reasons. When listening to the radio, I will listen differently depending on whether listening to the news, or listening to radio plays, or listening to classical performances and 'Late Junction' on Radio3.

I do listen to 'background music' when I'm cooking, but that is the only time and I will choose suitable 'music to cook to' (!)

In general, I think I listen to music from an overall perspective, regardless if it is live (concerts etc.) or recorded - that is the overall sound, though a lyric line of a piece of playing will 'pop out' unexpectedly.

Rarely do I listen forensically or analytically - music is not meant to heard that way; it is meant to move mind, body and soul. If I do want to listen 'into' a piece I will use headphones, but that is not my usual modus operandi.

When trying out a new component I listen to the overall sound, I do not listen for changes; any changes there are, if they are important to me will be heard without listening for them whether I want to or not.

Referring to the OP's citation of DSOTM: yes - I can tell the surface on which running footsteps are made, as I can tell you the material out of which the soles of the shoes are made - and possibly where the recording was made.