IPod Nano 3g no longer syncs (some) mp4 videos when they used to sync

iTunes 9.0.3.15 with iPod Nano 3g (1.1.3) on AMD Windows 7 64 bit
Videos which used to play on the iPod, no longer will sync to the ipod. They used to sync when I had Windows XP but after a disk crash and now using Windows 7 64 bit, they dont.
The videos play just fine in itunes, they just refuse to sync.
Some videos that I have do go, but there is no obvious difference between them (file names, formats, etc).
I have reset the ipod to factory.
item type mp4 video
Video
frame 320x176
data rate 256kbps
total bitrate 375kbps
frame rate 23 frames/second
Audio
bit rate 118kbs
channels 2 (stereo)
audio sample rate 48khz
Any suggestions as to how I can diagnose this, are welcomed.
...Lyall

Ok, I may seem like a noob, cos I am.
But, I did discover the 'create an iPod/iPhone' version' (right click the video file)
It creates a nice small file (about 30% of the original), in a location I cannot control and ends up showing me two identical entries in iTunes that I cannot pick the difference between without doing a 'Get Info' and looking at the filename!
Best of all, this nice small file has NO Video.
I failed to find any settings in which I could nominate the target device, after all, they all have different screen sizes, you would think I could optimise it for my devices screen size.
I even transferred the converted content (after finding it) to a real OS (linux) and mplayer spits about too many audio packets and vlc simply plays sound.
And Apple software is supposed to be user friendly...
...Lyall

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libavcodec 53. 61.100 / 53. 61.100
libavformat 53. 32.100 / 53. 32.100
libavdevice 53. 4.100 / 53. 4.100
libavfilter 2. 61.100 / 2. 61.100
libswscale 2. 1.100 / 2. 1.100
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handler_name : (C) 2007 Google Inc. v08.13.2007.
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creation_time : 2010-02-22 17:27:21
handler_name :
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