My analogue experience is only with vinyl. My digital experience is with CD, SACD, digital downloads of PCM (CD resolution and Hi-rez), and DSD. If I may be permitted a small boast I have a high-end turntable, cart and phono stage. Prior to that I would have said that digital is easily better. One has to go very far up the food chain for vinyl to sound superior. If you stop and think about it vinyl is a mechanical method, and has to be done very very well to catch up with digital. But now at the broadest generalisation I would say they are equal. They are different but equal.
I have several instances where I have a digital and a vinyl copy of the same music. My experience is that sometimes the vinyl is superior and sometimes the digital is superior. What I have discerned is this: in the early days of CD it was inferior. This was typically because they were issuing digital copies of music mastered for vinyl. Claudio Abbado conducting with the LSO conducting Le Sacre was a striking example. In the late 80s this was the Le Sacre to beat. I thought to 'improve' on that with the CD. Fail. The CD was crap. Then just last year the Sydney PYT (pretty young thing) put out a fabulous album (Don't Let the Kids Win). I thought to myself 'Andrei, why don't you support the artist and get the LP as well?' Feeling all noble I did just that. The LP was crap. Crappity crappity über-crap. Forty bucks down the dunny. The circle was complete and I am convinced the moral is the same. In each case the original finished product was mastered for a particular medium. Then the 'suits' get a cunning plan. A plan so cunning you could pin a tail on it and call it a weasel. They reissue the same music on a different medium but do no work - read spend no money - on making allowance for the different medium.
This is my long-winded way to say: it is a crap-shoot.
I have several instances where I have a digital and a vinyl copy of the same music. My experience is that sometimes the vinyl is superior and sometimes the digital is superior. What I have discerned is this: in the early days of CD it was inferior. This was typically because they were issuing digital copies of music mastered for vinyl. Claudio Abbado conducting with the LSO conducting Le Sacre was a striking example. In the late 80s this was the Le Sacre to beat. I thought to 'improve' on that with the CD. Fail. The CD was crap. Then just last year the Sydney PYT (pretty young thing) put out a fabulous album (Don't Let the Kids Win). I thought to myself 'Andrei, why don't you support the artist and get the LP as well?' Feeling all noble I did just that. The LP was crap. Crappity crappity über-crap. Forty bucks down the dunny. The circle was complete and I am convinced the moral is the same. In each case the original finished product was mastered for a particular medium. Then the 'suits' get a cunning plan. A plan so cunning you could pin a tail on it and call it a weasel. They reissue the same music on a different medium but do no work - read spend no money - on making allowance for the different medium.
This is my long-winded way to say: it is a crap-shoot.