Ipod Mini starts to sync then stops after a few songs and doesn't sync

It has been about a year since I synced my iPod mini (Generation One) with my G3 PowerBook Pismo. I have been using it with no problems but I wanted to ad new songs. I went to sync it and it wanted to update. I am on the latest iTunes. After the iPod updated it would start to sync get to song 7 and just stop syncing. I have to pull the iPod off and there is nothing on it. I have restored the iPod Mini several time. I even tried going back to the orginal disk. Nothing helps. I tried to repair disk permissions in Disk Utilities and that gets about half way through then has an error. I have to quit this operation and can't repair the permissions. Could these be related. I am not a mac doof but I feel like one.
Thanks for any help!!!
[email protected]

Try taking it into an Apple store, it sounds like a HD problem, or something. If you've tried to restore it, and that hasn't worked, taking it in is probably your best bet.
-Michael

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