HT1386 I'm reloading my music library onto my 5th gen.iPod nano and everytime it tries to sync a song (uncorrupted) it will take 2 hours to sync it 90% then it will stay there and not make any progress.  How to fix?

This has been going on for three days.  I had to restore my iPod because the artwork was scrambling around (anyone know how to fix that too?) and when I tried to reload all my music onto my iPod, it would load on a few songs, but then it would stop on "I Wouldn't Mind" by He is We, which I got off mediafire and never gave me problems before.  I unchecked the song when I tried to resync my iPod, and sure enough it just switched over to another song (this one being from a CD) so I don't think it's a file problem, but an iPod problem.  I've tried different cables, different USB ports, restarted my computer, uninstalled/reinstalled the latest versions of iTunes, even cleaned the lint from out of my iPod's docking slit.  I am using a Dell Inspiron which I got in October, and this is my first time restoring the iPod since transfering my library over from my old computer. 
Is there something I can do myself to fix these problems and have my iPod sync normally again??

as to rockmyplimsoul's post.
- unfortunately i don't really remember how i transfered songs to my MB anymore... it was several days ago and i didn't try fixing it until yesterday... after which point i've been through several bouts of struggling against smashing my MB/iPhone, pulling my hair, and punching my counter top several times until finally my girlfriend decided to go home and i quickly set about self medicating with alcohol - probably sounds funny, but true.  i'm sober now though! ;p  i think when i first went to sync my phone for the first time after resetting my MB, a message came up saying that i had songs on my phone that needed to be transferred to my MB or i would risk losing them during the sync session, so i clicked 'transfer'.
- i have a LOT of non-iTunes content.
- i have over 11,000 items in my itunes library (some of these appear to be sound effects that appeared in my library after i reset my computer - presumably stuff from garage band), and currently have 80 songs on my phone.
- my 'other' category is .86 GB
- i back up to iCloud
- i do use iCloud for other media storage.  mostly just reports for work.

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