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Regarding analog vs digital pressing. Rating the quality of pressings is case by case and there is no reason why a digital file can't sound great on vinyl.
Yes, obviously there have always been terrible analogue recordings, and rather fewer very good ones. There's still the potential that digital will never have because it cuts off a good deal of the sound, the foldover effect, and so on.
And certainly, even CDs can sound good--I was just listening to the CD transfer of 'Turn of a Friendly Card', and it's very good, but the original album is simply better. The highest echelons of analogue in the 70s were just amazing, and then much of that technology was thrown away for commercial expediency.
Regarding analog vs digital pressing. Rating the quality of pressings is case by case and there is no reason why a digital file can't sound great on vinyl. I think the response to the loudness wars is passing, its no longer necessary to get a vinyl copy of something not to have it brick walled.
I would be interested for example in hearing Kevin Gray remaster a digital album but I've no interest in anything Miles Showell is doing at Abbey Road where everything has to be digitised to work on the 1/2 speed cutting rig.
I like 1/2 of the MOFI roster for mastering and to me they all have a very strong signature sound. But I'm basically a Kevin Gray fanboy. His Electric Warrior and Astral Weeks are brilliant.