Problem with synching iPod 4th gen Nano to iTunes Vista 8.02

Not had a problem with this Nano - sometimes hangs on first play nothing a reset doesn't cure - til now.
For some reason iTunes decided a Smart playlist (To delete - if I rate one star it lists it there) was missing when it was there, just disappeared for a while. It eventually came back after I recreated it.
This meant the other playlists I synch from fell over and refused to synch to the iPod (having a massive collection and only a 8Gb Nano means I tend to have playlist for Recent stuff, and random shuffle type playlists).
So I deleted the condition in those Smart Playlists, and thought it was fine...nope, it now only synchs less that half of the iPod, even though the playlists have loads more tunes in them. Tried deleting the 'To Delete' playlist(s), restoring the iPod, upgrading from 8 to 8.0.2 - no dice. Even a restart and an iPod reset doesn't fix it.
It just says 'synch complete' when there are obviously many more files to download, it usually only does 300-600 then stops. Sometimes it tells me (wrongly) there is not enought space on the iPod by 0.2 of a Gb or something, and says it won't synch. When I reduce the size of one of the playlists, it then goes back to saying 'Synch complete'.
Don't know what's wrong with it - could it be the iTunes library - I moved it to an external USB drive, and switched from my XP machine to this one, but it seemed to be working fine? Hence the restart - I had switched off the drive when I put the laptop into suspend mode, so initially it wasn't there, so I thought iTunes might have gotten confused, and did a restart after upgrade. Still the same.
Any ideas?

Nope still doing it. Just got to 2-thirds full.
So what's happening now it says
'Ipod cannot be synched, playlists are 1.82Gb and there is 1.77Gb on the iPod'
Fine, you then reduce the size of one of the playlists by say 100-200Mb:
Then it doesn't sync those files - it doesn't sync anything and says 'Sync completed' and 'Ok to disconnect'
Argh.
BTW what's sentinel?

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