Installer deleting songs, not installing

Ever since I got my iPod, I've had problems with updating music to it, but mainly when trying to update with more than 100 songs. Recently, I updated to iTunes 5, as well as updating my iPod software. Now, it says that it's loading the new songs, but freezes in the middle, and when I disconnect, it has removed songs rather than uploading them. Anyone know what is the cause, and the solution to this problem?
Thanks

Ok, I got around the problem, here's what I Did:
Make iPod update manual
Then load only a few songs at a time (no need to delete any as it won't make duplicate songs)
go through your list of songs until the end
after thats done, include the play lists you want
Now I have all my songs and playlists.

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