I know we all know the problems with iTunes. But this is so odd.
Seeing this a lot recently due to not understanding iTunes Match or iCloudTunes or whatever it's called. I have to go into the store to find a song I know I have. I have to click to "buy" the song, it asks me for my password (again) and then it says, "You have already purchased this item. Would you like to download it for free?"
Considering the interaction pattern knows I was attempting to pay money for it, I think they could safely assume I'd be happy to download it for free.
And then to confirm that I have to click "buy".
I know this stuff takes lots of work, but this feels so wrong and pretty straight forward to fix. It's not complicated, it's just hard.