Strange iTunes Transfer Problem

Hey all, first time poster.
Not sure if this is the correct section for this, so I apologize in advance if it isnt.
Currently running iTunes 7.5, but the problem I am having existed prior to upgrading to 7.5.
I have 1200 or so songs (mp3 format) and 19 tv shows i purchased from the iTunes store. I was originally using an 8gb ipod nano (2nd gen) and recently purchased an 80gig ipod classic. iTunes automatically recognizes the ipod classic or nano when they are connected to the pc and automatically begin to sync when connected.
The strange issue I am having is that iTunes did not transfer all the tv shows, only 15/19 to the ipod classic. All episodes are checked for transfer in iTunes, so i'm not sure why they havent all transferred over to the classic.
A second problem I am having is that even though I have album artwork in iTunes for every single album I have, only SOME songs show album artowrk, and others do not. For example, the album artwork will display for one song, and not on another song, both from the same cd. This issue is happening both on my nano and my ipod classic.
Any ideas? Thanks in advance for the help!

jusion,
This can happen with shortcuts created by Windows installer sometimes with iTunes or other programs.
You should be able to create a new shortcut to iTunes.exe in Program Files, put it where you want, and delete the ones you don't want.
Hope this helps,
Nathan C.

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    Im trying your method right now, when im finished ill let you know how it worked out. I agree with your comment on apple needing to pull the latest version and get a version that actually works.

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