IPod Classic won't display artwork, delayed gap when playing songs

Hi there,
Recently I had my computer wiped and upgraded from Windows XP to Windows Vista (Ultimate) The music and iPod were both originally synced to the XP version, Upon reinstalling iTunes on my computer and placing the songs stored on my external hard-drive in my iTunes library and re-syncing my iPod Classic I have found that artwork will not display on the songs (it does display in the side view when browsing through albums though.) along with this whenever I choose a song to play on the iPod there is a long delay with the iPod loading and even just skipping a songs, which is even more annoying, Along with this when I sync my iPod or go to update it, it crashes iTunes
I have tried restoring my iPod countless times, I've enabled disc use, disabled disc use, browsed over and over at the settings and preferences, restored the iPod, reset it, reformatted the iPod, reinstalled iTunes, defraged the iPod (I know its not recommended) performed a disc check on the iPod (which there are apparently no errors) I originally believed it to be corrupted but went through the necessary steps to fix that, I'm at wits end with the thing, any help?
I'm pretty anal when it comes to my iPod being all organised so this is a massive bother to me lol.
Cheers for any help and suggestions,
Phil

Probably, the easiest way to resolve this is to copy the artwork from one song on an album and paste it into every song on that album.
In your iTunes Library, choose an album that has artwork issues; choose one track that has the artwork and copy it. Then:
the slightly longer method is to check each song individually, until you find the one with the missing artwork. Paste (the copy previously made) from one of the other tracks on the album.
a slightly quicker method is to highlight all the songs on that album (make sure it is just that one album) and paste the artwork into the box.
Sync the iPod with your iTunes Library.

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See
iOS: Device not recognized in iTunes for Windows
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or
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See Corrupt iPod classic.
tt2

IPod Classic won't display artwork, delayed gap when playing songs

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