I've spent an eternity trying to get my vinyl rips to sound like the original vinyl. I've owned ADCs from Pacific Microsonics, Prism Sound, RME, Tascam, Korg, MOTU, etc. There's something about the original vinyl that my vinyl rips seem to miss. However... I'm not sure if this is down to the recording or the playback process. Perhaps a bit of both?
If I were to guess as to a fundamental flaw in digital (if indeed there is one), I'd say that it might be digital's noise floor being modulated by the music signal. But this is pure speculation, as I'm no electrical/digital/RF engineer. That's why I much prefer using real music and nulling techniques over test tones (sines, squares, impulses, etc.). Impulses are especially useless as they're not bandlimited, and could never occur in any music signal you ever feed your DAC (they would have been filtered out by the anti-alias filter during ADC). But getting nulling to work correctly is fiendishly difficult.
Although I remain less than 100% content with my own vinyl rips (because I can compare to the original), I'm totally content listening to digital via CDs and Roon/Qobuz streaming. Many albums sound absolutely stunning to me.
Mani.