ITunes won't update the songs on my iPod

I have a 20G iPod, purchased in Nov. 2004. For the last several months, the iTunes software has been slow to recognize the iPod and start automatically updating songs (it often took several minutes), but until recently it eventually recognized the iPod and went ahead with the update. Around October, the iPod started to freeze frequently when connected to iTunes, but I was able to solve the problem by resetting it. After resetting, the songs on the iPod would update successfully.
But when I tried to update the iPod after letting it sit unused from mid-December to mid-January, the real trouble started. I tried to do an automatic update and the iPod froze. I reset it and tried again, but the same thing happened. I downloaded the latest version of iTunes and updated the iPod software, but the problem didn't go away. So, I restored the iPod.
At first, this seemed to make things worse. The iPod wasn't recognized by Windows. I solved this problem, but I don't remember exactly how...I managed to get Windows to recognize the iPod somehow, then had to follow the instructions in the Apple website's article entitled "iPod appears in Windows Explorer but does not appear in iTunes" in order to get iTunes to recognize the iPod.
I thought this had solved the problem -- the iPod connected to iTunes and appeared to be updating normally. But when it said that it was finished updating, only a couple of Podcasts had been transferred to the iPod. None of my songs were there, and most of of the Podcasts weren't either. I tried updating again and noticed that although it said it was updating, the songs just went from being qued (with the little grey round waiting-to-be-transferred symbol to the left of the song title) straight to supposedly being on the iPod. None of the songs ever had the little orange round in-the-process-of-transferring symbol next to them.
I tried clearing all of the songs in iTunes and then adding them into the library again, but that didn't do anything. I don't know what else to try. I'm very, very frustrated at this point. Does anyone else have some experience with a problem like this?
IBM ThinkPad Windows XP
IBM ThinkPad   Windows XP  

Thank you both for the suggestions.
I plugged the iPod into my computer this afternoon and opened iTunes. iTunes gave me an error that I haven’t seen before – it said “iTunes cannot read the contents of the iPod “Kathleen’s”. Use the iPod software updater application to restore the iPod to factory settings.” I ignored the advice, closed iTunes, and tried the fix suggested in the page linked to by b noir (that is, reassigning the drive letter). I then opened iTunes again, and I got the same message. I then tried resetting the iPod, which was saying “Do Not Disconnect” continuously, unplugging it, and restarting the computer.
When the computer started up again, I plugged in the iPod, then opened iTunes. I then let it sit there and “think” for a few minutes. The iPod said “Do Not Disconnect”, and after a while iTunes came up with an error message. The window was called “Device Timeout”, and it said “The requested operation on \Device\Harddisk1\DR3 was not completed before the time-out period expired.” Cancel, try again, and continue were my options. I chose cancel. Then iTunes gave me the “iTunes cannot read the contents...restore the iPod” message again. So, I restored the iPod, figuring the combination of reassigning the drive letter and restoring the unit might do the trick. After restoration, iTunes recognized the iPod again (that is, it didn’t give me an error message), and started pretending to update the songs on it, but none of the songs actually went onto the unit (i.e., I had the same problem as before).
I’m not sure how to try Mary Beth’s suggested fix, as I haven’t got any playlists except the ones automatically generated by iTunes (90s music, Top 25 played, etc). Is there anything else I can try?
IBM ThinkPad Windows XP

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