Ipod Classic Randomly Loses Tracks/Songs when sync with Itunes

My IPod Classic Randomly loses Songs from playlists. I can sync with iTunes and it will keep say 8 songs out of 10 in a playlist (sometimes all 10 if I’m lucky) but if you re sync it will have 7 or 9 different tracks in the playlist. Its Very annoying as my girlfriend uses it for teaching and songs are always missing.
I have tried updating IPod, re-installing ITunes and restoring IPod
Any Ideas??? Apart from buy a new one but from what I can guess seems like a software issue.
Thanks

I was having the same problem.
I have an i pod classic 80GB (with the wheel) I think it's 5th generation
I would start a Sync, it would sync 2 or 3 songs then stop or hang up, which did not interfere with any other function, so I would not say it froze.
Once I ended the sync by clicking on the X next to the sync progress bar at the top of the window, I ejected the ipod and then plugged it in again. Then I selected my i pod under Devices in the menu on the left-hand side of iTunes. Clicked on the summary tag. Clicked on "Manually manage music and videos" Clicked ok and apply.
When in manual mode, you cn drag songs from iTunes to the device icon in the sidebar. Once I downloaded the song or songs or album that was causing the problem, I then unselected manual load, and everything else was able to sync normally on automatic mode.

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