Help - My 30 GB Ipod only downloads 342 songs...

I have about 490 in my itunes Library, but everytime I go to update my Ipod it downloads 342 songs and then gets "stuck" on 343 and then starts making a grinding noise and freezes up. So then I have to go through the restore process only for it to happen again....and again....and again....and always gets stuck on song 343. I have tried every possible way to download the songs including manually and even by individual song, switching orders that I upload them, etc. But no matter what, #343 freezes it up.
Suggestions please. Thank you in advance.

Okay, then let's try a reinstall of iTunes.
(Although you may have downloaded iTunesSetup.exe again onto your computer, it's not the same if you didn't remove iTunes+QuickTime off your computer using the Windows Installer CleanUp Utility first. So try proceeding onto a full reinstall of iTunes here):
Disconnect your iPod from your computer.
Go to "Add or Remove programs" in Control Panel. Find "iTunes" and "QuickTime" on this list, and remove them both.
Then, download the Windows Installer CleanUp Utility, to clear out the remaining iTunes and QuickTime installation files off your computer (see this MS document for information on it):
Description of the Windows Installer CleanUp Utility
Also, use this article to manually remove the left over files from installation:
Removing iTunes and QuickTime for Windows
After you've done that, restart your computer.
Then, go to this page to install the iTunes + QuickTime installation pack onto your computer again:
Download iTunes - 7.1.1.5
Now, restart your computer once more.
After the computer has fully loaded up, open iTunes, and connect your iPod to your computer.
Try automatically syncing it with iTunes again, and see if it works or not.
-Kylene

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