A significant and underappreciated factor is psychoacoustics. We listen to different types of music depending on the mood we are in (knowingly or unknowingly). We approach music differently as well: sometimes anything sounds just great, sometimes we find something to nitpick with anything we play. That is all regardless of system/SQ. The different sound impressions have more to do with my state of mind than the gear.
I have noticed that with better systems, new aspects of the same recording are coming through. Usually with music I already like, such as post-punk/avantgarde (and also some punk) and those records may not be considered "audiophile". I have been surprised more than once by the sophisticated recordings by such "unsophisticated" music.
I have also trained myself to instantaneously switch from analytical listening to appreciation listening. I like to write music "reviews", particularly of newly released music, where it helps to quickly switch between those two modes. At one point I listen to the frequency of syncopated beats in relationship to long line elements and measure break, mode changes and chords employed, then just listen how the ensemble washes over me. With classical (mainly baroque music for me), I listen for trills starting at top or bottom, what kind of trills/ornaments, intensity of messa di voce, and type of bowing used (I am an amateur viola d'amorist), and then just listen for the how it all comes together.
Continue enjoying your music!