At a loss for a solution

I've been at this since Wednesday. Five days now, for about 4-8 hours a day.
The low-down-
-on Wed. I updated to iTunes 5 from 4.9. When 5 started up I connected my iPod and was told that I needed to update my iPod software, so I did from v2.2 to v2.3. Then iTunes 5 begain to update my iPod with my iTunes library. It got to around song 280 and freezes up on me with the info window in iTunes stuck flashing between "updating iPod do not discounect" and "uploading song 280 of 2154: Name of song" From here I've gotten different error messages here is what they were.
1-"attempting to copy to disk "Ricky Woodson's iPod" failed. The disk could not be read from or written to."
2-"Some of the songs in the iTuens music library including the song "name of song" were not copied to the iPod, because they could not be found."
the first message is the one I still continue to get. I've changed all my songs to Mp3s and deleted all none mp3 files.
I've called apple and they've had me do everything from delete and re-install to restore my iPod, to deleteing my entire iTunes library and then going to iTuens File menu and then "add to library" and then select my entire harddrive. iTuens then imported all the sounds off of my harddrive. This still didn't work. Then I found a thread on discussion forums where someone said I should delete the iPodDriver.kext from extensions, so I did. Then I couldn't get my iPod Updater to see my iPod when it was plugged in. I had to get pacifer to download the iPodDrive.kext extension file agian (reinstalling iTuens and iPod updater did now install the software)
Next I did an arcive and install of my OS system, which is Tiger by the way.
Then I update all my software and re-install iTunes and the 9-9-2005 iPod updater and give it another go...still no luck. But now I can use the restore button in iPodUpdater to wipe my iPod
In my last ditch effort I even tried to erase my ipod using disk utility and then restoring the software using iPod Updater. Nope this didn't work either. I'm in need of help. I'm willing do try anything because basically my iPod is worthless now. reduced to being a highly designed over priced paper weight. These problems only begun the day I upgraded to iTuens 5 and iPod v2.3 and Quicktime 7.0.2 Someone please help.

Hey Ricky,
I've sorted my problem out but I wouldn't exactly call it a solution. I'll run through all the steps I took... not sure if you need to do all of them, but just in case... and hopefully you'll be able to sort yours out too. I think it's actually problem with iTunes 5 which they haven't sorted yet. Anyway, here's what I did.
1) Removed all music from my library on iTunes
2) Uninstalled iTunes
3) Restored my iPod using the latest updater
4) Reinstalled iTunes
5) Added music back to library
6) Set it to "Automatically sync with the iPod" (I normally just drag the library over to it)
7) Connected up iPod and it started copying over songs.
8) When the error message "Attempting to copy to the dish Simon's iPod failed. The disk could not be written to." obviously came up again! I clicked ok and waited for it to say it was ok to remove the iPod. I then disconnected iPod for 30 secs then reconnected and it started syncing again from where it had left off. This happened again about 7 times but repeated the steps each time and eventually got all music (with artwork) on the iPod. Although 7 times is still not great, it's better than the 50 times I had before... this is for 4000 songs so it may happen more or less for you.
I definitely think this is a screw up in iTunes. As you can see this isn't really a solution but a temporary fix to deal with their screw up! I can't believe they don't get rid of all the bugs before they launch software. Anyways, I hope that helps you in the short term. Be sure to let me know if you find anything more long term! Good luck

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