ITunes / iPhone will not allow transfer

So I select a playlist and try and drag it to the icon of my iPhone in iTunes. When the mouse hovers over it, it forces the iPhone pull down to display the onboard categories. However I get no green "+"and nothing transfers.
Yes, it is set to manually manage
No, none of the files are "not readable" by itunes or ipods.
Yes, I tried restarting my iPhone and iTunes.
Yes, I tried reinstalling iTunes.
Yes, I have run all updates. They didn't fix the problem.
No, I have not restored my iphone. My friend ran into the same problem and doing so didn't fix it. So I'll save myself the hour and a half it would take to reload all my content.
If anyone else has any idea whats up, please let me know.
-Rev-

Syncing would have the same effect as restoring. I'd be sitting there for an hour waiting for everything to reload.
But that is kind of beside the point. i shouldn't have to sync. It allowed drag and drop before, hundreds of times. It should do so again.
But thanks for the thought.

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