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As I’ve discovered since
As I’ve discovered since I’ve been getting older most music doesn’t age well. Doubly so for “indie” or “underground” music which exists in part as a statement on the time it was made in. (@smevans: that includes the Pixies, imho)
The only thing you can do is weed out your collection every six months or so. Me, I consider everything in it a candidate for removal unless I’ve decided otherwise - which is rare. So every time my iTunes collection gets over, say, 4GB, almost everything in it goes. Unless it’s on a playlist marked “keep”.