Sync Problems With Ipod and External HDD

Ive just got a new 4G ipod after returing it because of HDD problems and when i try to sync with itunes, it manages to sync a random number of songs (ill get to that later) often about a 100 and the says "Ipod could not be written or read from". The thing is that i use an Lacie 80Gb External USB 2.0 Powered Harddrive as my Music library. Also it seems not to be USB timeout because ive tried to power both the External HDD and Ipod with an external powered USB 2.0 Hub. Ive found out that the number of songs that syncs each time depends on the songs, because it seems that some songs cannot just be copied (ive tried to copy them through finder and it dosent work either, but moving and/or deleting them works) and they arent in anyway different(what i know of) to the songs that manages to be synced to the ipod. None of the songs have any kind of DRM restrictions.
Ibook G4   Mac OS X (10.4.7)   Use An External USB 2.0 powered HDD as main media storage

Ive had it on my Ibook before and then moved it to the HDD because of Space Shortage, and then just added as ive aquired more music. Idon't Really Remeber but i think it worked before without any hiccups. oh well otherwise i can just delete those files because theyre only single files here and there. but its quite irritating because they don't seem to have any kind of corruption.

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