I actually did not understand the point of your OP. Why would you stop “getting into” certain songs if you upgrade?
The point I was trying to get over is that the experience being absorbed in music doesn't necessarily depend on sound quality. Another way of putting it would be suspending disbelief. Once I'm pulled into it, I may not care about quality because I'm just enjoying the music.
Very likely improved sound quality will make it easier to get there or make a wider range of music accessible. But still not necessarily enhance the experience of listening.
Of course, this may be different for difference listeners.

