ITunes doesn't sync all my songs.

I've put some of the songs from my computer to iTunes, plugged my iPod Touch into the computer, iTunes has recognised the device, I've clicked on my iPod, gone to 'Music', selected 'selected playlists, artists and genres', 'include music videos', 'include voice memos' and then I've selected the artists and playlist I want to go on my iPod, then clicked 'Sync'. Out of the 165 songs in the playlist I synced, 11 songs haven't synced to the iPod, and about 5 or 6 of the different artists I selected haven't synced to the iPod. A few of the artists/songs, I've been able to sync before, whereas some of them, I have tried time after time and they've never been synced, but since I updated my iPod and iTunes, through iTunes, they're not all syncing.
So I went to www.apple.com/support/ipodtouch/assistant/ipodtouch and searched all over apple's support pages, but could find nothing to help me, even though there was mention of help with syncing problems on the iPod Touch support page (underneath the link from said page to the troubleshooting assistant it said 'resolve common syncing and network issues and more' but all it gave me on those pages was the regular advice, which I'd already tried, like restart the computer, check the USB port, ect)
Any idea why I'm having these problems?

A video that previously synced now isn't, also.

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Winston Churchill Poulton-le-Fylde, UK
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While navigating through other threads looking for similar problems, I found this reply from Winston Churchill:
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ITunes doesn't sync all my songs.

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