Music on library grayed out/Itunes purchases being made twice

Songs are grayed out on my Itunes library. They were deleted from my Nano when I synced it, and I can't put them back on. I tried deleting one of the songs off my library and re downloading it, but Itunes just charged me for it a second time. This isn't the first time I've been charged for a song that didn't actually end up on my library. I want to find a way to get the grayed songs back on to my Ipod and get my money back for the songs I was never even given.

Is the computer authorized for the Apple ID that the content was acquired with?
Is the device backing up to iTunes on the computer or iCloud?  If backing up to iCloud purchases do not automatically transfer, the user must manually select Transfer Purchases.

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