ITunes freezes when trying to add songs to 30GB video iPod

Here's my situation exactly:
I just bought a 30GB Video iPod with some songs and videos already uploaded onto it. After much reading, I found out how to get the songs from the iPod onto my computer so I could put them into my iTunes library. I added some songs and videos of my own to my iTunes library and tried to update my iPod. The iTunes program says do not disconnect-- updating iPod but my iPod doesn't say anything. The funny thing is that the actual iPod says do not disconnect until I open iTunes and try updating it, then the do not disconnect msg goes away on the iPod. I left my computer on for about 12+ hours straight while iTunes said Do not disconnect.. woke up the next morning and iTunes was frozen-- no new songs on the iPod. What could the issue be exactly? I have slight issues with my usb ports-- for example; sometimes they do not recognize things plugged into them (memory sticks, printers)... BUT it does recognize my iPod-- it shows up in my computer as a removeable disk drive or something, plus as soon as I plug it in the iPod says do not disconnect. I definitely need help though... I'm dying to put some songs of my own on this thing.
Things I have tried so far:
Deleting and installing iTunes and everything else again
Restarting computer and iPod-- of course
Tried plugging it into diff. usb ports
HP Pavilion Windows XP

I'm assuming the usb hardware problem may be a good possibility because I've always had problems with my usb ports. I can't get a printer to work or those Scandisk things. My assumption is perhaps u can take files from things plugged into the usb ports but you can't add files/etc to things plugged into the usb ports. I will still attempt what you told me to do. I just don't want to lose what I currently have on my iPod and be stuck with a blank iPod because I use it quite often. Maybe a new computer should be my next purchase? Thanks so much!
HP Pavilion Windows XP

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ITunes freezes when trying to add songs to 30GB video iPod

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