Sometimes better quality in sound does not mean more artistic enjoyment. Dimmu Borgir's Stormblast, when re-recorded, lost a lot of 'artistic hook' if you may.
Since enjoyment is tied to the sound, not the objective quality of the recording, I think that having a system that is agnostic is the best way to go. You get whatever is recorded and yours is the choice for this or that version.
I'm not unaware of using what is traditionally considered a lower quality as an expression. I thought I'd manage to convey that when mentioning lo-fi as an example, but obviously I was wrong. Some records were deliberately made noisy or messy or otherwise. The Artist was deliberately made B&W. You might be surprised but I do understand such simple and basic concepts. I'm not that stupid.
But all my questions still remain. It is a minority that wished for poorer quality as an expression. Very often you have artists themselves in charge of reissues making it obvious they wished for something more. How about a quiet passage on the "Summertime" by Armstrong and Fitzgerald with a loud crack (just an example). You think it was an artistic expression for them? I doubt that.
Anyway, I don't see much risk in this since I don't think the Dimmu Borgir's (or Fallen Angel or any of the other you mentioned, the Blasphemy, you don't have to keep changing the example) audience is waiting for a high quality release and I don't think Diana Krall's audience is waiting for that either.
Sure, you can poise a question on artist's intent, which would be fair, but honestly, superfluous in most cases. I'm often in studios watching people compromise and shrugging, saying well since that's the best we can do, let's just record it like that.
Finally, all said and done, I don't really think it's fair treating something mediocre as someone's intent. It's like... insulting. Maybe what you hear is not what he had in mind. Maybe it's just what he could afford.