Comparing "digital" en masse to "analog" is equivalent to comparing karate to jiu jitsu. Which is better?
The answer: well, you need no answer.
The better prepared, stronger, fitter will always win.
When looking at equivalent levels of mastery, then the answer is: each are specialists of something. Do you want to knock out your opponent, or restrain him?
Digital tend to be more suitable for bigger groups of people, A/B evaluations, getting a good show, listening to the latest recordings, short sessions.
Analog is more suitable for finding the substance, lone whole night listening, touching soul an spirit, invoking memories that you thought were gone forever with force that takes away your breath.
Digital wants you to focus on the virtues of your gear. Analogue lets you flow with the music.
Of course, poor digital will focus on the weaknesses of your system, and poor analog will annoy you with issues you do not have with digital.