Can't put ripped DVD files onto iPod

I've ripped a couple of 1.5hr video files to MPEG4 format using Xilisoft's DVD to iPod software (very good by the way) but I can't get these files onto my iPod (I've checked them in Quicktime and they look fine).
I've tried importing into the library then manually dragging and dropping, but they just won't copy (I don't get any warning message either). Syncing doesn't work either.
Anyone got any ideas?

What exactly happnes when you try to sync?
Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
Do the songs play in iTunes?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod
Did you set up the iPod on this computer?

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