Unfortunately adding some files still didn't solve the problem. We can
see that the songs are being uploaded, but I'm guessing the database
isn't being updated (I can only see the 3 songs from iTunes in Rhythmbox
and on the device).

$ find '/home/dcoles/.gvfs/dcoles’s iPod/iTunes_Control/Music' -type f
/home/dcoles/.gvfs/dcoles’s 
iPod/iTunes_Control/Music/F05/Sorcerous_Stabber_Orph~FQ.mp3
/home/dcoles/.gvfs/dcoles’s iPod/iTunes_Control/Music/F11/ZDFQ.mp3
/home/dcoles/.gvfs/dcoles’s 
iPod/iTunes_Control/Music/F14/B06%20-%20Stickerbrush~BW.mp3
/home/dcoles/.gvfs/dcoles’s 
iPod/iTunes_Control/Music/F18/B03%20-%20Donkey%20Kon~IC.mp3
/home/dcoles/.gvfs/dcoles’s iPod/iTunes_Control/Music/F28/ZADL.mp3
/home/dcoles/.gvfs/dcoles’s iPod/iTunes_Control/Music/F31/07 Viva la Vida.m4a
/home/dcoles/.gvfs/dcoles’s iPod/iTunes_Control/Music/F34/01 - UNDO.mp3
/home/dcoles/.gvfs/dcoles’s iPod/iTunes_Control/Music/F35/EMQO.mp3
/home/dcoles/.gvfs/dcoles’s iPod/iTunes_Control/Music/F39/03 Samuel Barber - 
Ada~KT.mp3

I'll report this upstream.

-- 
Music synced to iPod touch does not appear on device
https://bugs.launchpad.net/bugs/553301
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