I recall reading (maybe here?) that iTunes is typically developed by a team of about two devs at a time(presumably the actual interface part - obviously lots of people working on bits and pieces in the background for various functions like encoding), and that’s it. And, because no one likes it, it’s a bit of a red headed step child that gets robbed off to whoever was too slow to say “bags not” when it comes up. Seems weird for such a big company, but it makes sense if you consider how bad it is, and the weird total-change-of-metaphores that occurs between versions.
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