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The issue with poor remasters is why I've returned to the first CD version of my albums whenever possible if the original sounds better than the remastered version. In some cases the remastered version might be better, such as with early CDs mastered from digital recordings back when the Music Industry was learning the proper techniques involved with digital recording. Also, a few times the original CD release might have been edited and the remaster restores the part that was edited out.
When it comes to vinyl, it's my opinion that it can sound better than digital as long as: (1) it has only been played a very small number of times, and (2) it is played via well-adjusted high-end equipment. To me, another important difference between analog and digital is that: analog has the potential to be continually tweaked for improved sound quality, while digital is perfect within its standard but it is limited to that standard.
I think another factor in the sound quality of old recordings is the way they were originally recorded and then mixed. An example of this are the early Beatles recordings. One of the controversies about the original Beatles CDs was that the first four albums were released in mono rather than stereo. If I remember correctly, although the original recordings were done with two tracks, the vocals were recorded on one track and the instruments on the other and then they were put together for the mono mix to give it a better sound. I've had a few recordings where this appears to be the case (but the tracks weren't put together for mono) because I hear the vocals on one side and the instruments on the other.
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