There are two ways to get improvement.
First would be to get more of the better sound. Say upgrading cables over the white and red variety.
Second would be removing the bad, irritating sounds. Like those little speakers that boost up the bass with the annoying thump. thump to give the illusion of more bass.
So even if a system does not sound high-end (lots of "good sound") it still can be enjoyable because it doesn't have the "bad sound" to annoy you. Some hi-end you just hear too much bad with the good.
Could one reason that analog sounds better because although it may lack in "if you want to define detail as good sound" it also lacks in "bad sound"?