It’s a complex issue. There were a lot of analog to digital transfers that were poorly done (I think this more prevalent in pop than Classical). The playback equipment of the time wasn’t the culprit as much as the transfer engineers. The playback equipment has improved, but I have read several interviews with recording engineers who all say that as time went on they became more comfortable with digital.
The irony is that as transfers and playback equipment both improved, that’s when the lp resurgence happened.
The music is the thing. If comparing different technologies is interfering with enjoyment, and one can’t stop making comparisons, then either:
1) Admit to yourself that listening to gear for the sake of listening to gear is an enjoyable end in and of itself; or
2) pack up either the digital or analog system and keep it out of the system for a while and see how you feel about after a few months