This is my hands-on experience as well -- in fact I recently discovered that there is much in digital that is, or can be, off. The little things, that do not always make an earth shattering difference in good analogue.(...) a little off with digital is way off. more limited than analog so we hear system set up easier since wrong is more prominent.
Like signal tansfer, for example:
my DAC is, reportedly, one of the best sounding available: so, one could say, the digital signal processing part is OK. I also have high-erformance re-clocking device which, I thought, should complete the digital reproduction puzzle.
I was wrong.
Lately I discovered that in digital, processing the file isn't enough... you need to address signal transfer as well.
I inserted a USB isolator between streamer & DAC -- in other words I addressed the signal transfer part of the digital equation.
The improvement is astonishing!
Remember: nothing else changed, I only added a device (and an extra cable)
Analogue: at one point I rewired the arm using a reportredly ultra-resolving wire, with no mid-way termination, so the arm plugs directly into the riaa. The result was better resolution and instrument separation... probably. If it's there objectively, it's subtle.
Low quality LPs (ex: low-cost Italian pressings from the 80s) still sound just as horrible.
Please excuse the rambling -- but this contrast is an often overlooked quirk