It may not be the recording, but the mastering. At least on vinyl (I can't speak to CD or digital formats), I can play some standard reissue of an old pop album that sounds flat and lifeless; but find the right early pressing and even if the original recording has its warts and limitations, you get the breath of life in it that doesn't exist in the mediocre remaster/reissue. These differences are not subtle and involve no 'golden ears' beard stroking contemplation. The differences are pronounced and readily apparent. That then means that you have to research the best pressings, or buy a bunch of them and make that determination for yourself. I have to assume the same issue exists with CD/digital formats.
I'm at a point where I'm in it for the music, not for the sonics- but that said, I still seek out the best pressings of the music I'm interested in. It may not make as much difference for newly released material where the recording started in the digital domain, a lot of dynamic compression was used, and there isn't a wide range of options for different masterings. But, certainly for older stuff, there can literally be hundreds of different versions of a popular recording, issued at different times, from different places (both within a given country and across the world).
Some recordings just didn't start out that great to begin with, so even the best versions (on vinyl) have their limitations. I don't mind that, though I hear the shortcomings. But, there is some distance you can go to improve the source material that has nothing to do with the gear, once your system reaches a level of 'good.'
