Cannot sync iPod with iTunes and "Other" data increasing

So here is my issue:
Since I updated my iPod to v1.2.3 (or whatever the most recent one is) my iTunes will give me an error message when I try to drag+drop files from my PC library to my iPod (error message 48). Now when this happens I'll get the error message but iTunes will keep transferring the files I wanted to add to my iPod, BUT instead of them showing up in either Music or Movies the tranferred data just adds to the "Other" section. And I don't know how to view/delete "Other" files.
Is the only answer to restore my iPod? And if I do this, won't I just have the same issue when my iPod is re-updated to the most recent version again?

If the iPod database gets corrupted, it will add files to "Other" instead of where they really belong.
Restoring the iPod will erase this database and recreate it.
And if I do this, won't I just have the same issue when my iPod is re-updated to the most recent version again?
No, it shouldn't. This is why you Restore the iPod. It erases the corrupt database.

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