For me it depends...
- on the kind of quality issue: pop & crackle, thin-sounding old recording etc. I can live with (ex.: Django Reinhardt) Brickwalled recordings, hardly. And while DR is not the be-all and end-all, a quick check at the DR Database or running the checker will give me a pretty good indication how it will sound to me during actual listening....
- on the level of the quality issue: for example a 7-8 on the DR range doesn't bother me, I'll tolerate even 6 or so if I like the music, but after that... For some vinyl rips, if the person didn't clean the record and didn't bother with even a basic de-crackle, it can get pretty distracting.
- on how much I like the music... duh. But actually I find that "old" CDs I bought during my youth (which coincided with its beginnings) sound better now (on the fanciest equipment I have owned since those days) than most modern "remasters" : p
A specific example of going over the edge: I quite like Florence + The Machine ever since a friend made me discover Lungs at that time. Now her style has a bit of bombast, and the album wasn't the greatest in terms of DR. But it was perfectly OK, wouldn't stop me from listening to it many times.
Then Ceremonials came out, was looking forward to it, listened to it and thought yeesh. But I really wanted to like it and gave it a couple more listens. And haven't listened to it since then apart from rarely 1-2 songs. I cannot bring myself to listen to the whole album... it's already all bombast without the variation present in Lungs, but then the total brickwall mastering took it far over the edge, intentional or not. Interestingly, even "non-audiphile" reviewers who liked it commented on how some of it was almost too much for prolonged listening (without framing it in terms of another Loudness War victim)
In a similar vein, NZ singer Kimbra's somewhat over-produced studio album is actually borderline OK, but some of the "live" in-studio tracks (and an outdoor one) so much more compliment her talent that I'll take the compressed audio extracted from the HD YouTube vids (and background noise), warts and all, any day over the same songs on the lossless CD-rip...
Edited by TheGrumpyOldMan - 1/19/13 at 9:45pm