My ipod touch 3rd gen will not sync to pc.itunes file menu sync my ipod is greyed out

my ipod touch 3rd gen will not sync to pc.itunes file menu sync my ipod is greyed out.and i cant sync or put any new songs.please help me.

I've gotten the iPod to sync after restoring it and not changing ANY of the music sync settings.  I didn't even click "sync music", I just have it on manual and clicked autofill. 
After it synced all of the music successfully, I tried to sync a playlist (my recently added), and it's gone bonkers again, it won't sync the playlist's music, or any new music now. 

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