IPod not syncing on Windows or Mac

My sister recently purchased a Macbook. I tried using her iPod to move her songs from her PC to the new Mac (as mentioned elsewhere) but it didn't work. I ended up just wiping the whole ipod and moving songs with a USB travel drive.
When I synced up her ipod to the Macbook, I restored it to format it for Mac. The songs started to load and about 3/4 of the way through her library I received this error message.
"Attempting to copy to the disk <ipod name> failed. The disk could not be read from or written to."
I have tried using the "Disk cannot be read" troubleshooting page, but none of these suggestions help - it is a brand new Macbook - she literally bought it yesterday, and I have tried to use both a firewire and a USB cable that work fine with another ipod and computer. Disgruntled, I tried hooking up the ipod again, once again restoring it since data categorized as "other" was showing up on the iPod on the iTunes summary page. Once again, a few songs in we got another error message.
"The iPod <name> cannot be synced. The disk could not be read from or written to."
I have restored the iPod on the Macbook three times now. Each time, it goes through restore, and then when it is syncing with the music library it gives the error message as above, iTunes freezes and I have to either forcequit or manually remove the ipod.
Giving up, I figured I'd just load the songs onto the iPod from the PC. So I reformated/restored for Windows and synced up the iPod. The first error message I got was:
"The drive is not ready for use; its door may be open. Please check drive F: and make sure that a disk is inserted and that the drive door is closed."
I unplugged the ipod and there was only one song on it. I plugged it back in and it started to sync only to give me this error message a few minutes in.
"Attempting to copy to the disk <name of ipod> failed. An unkown error occurred (-53)."
Now iTunes on the PC is frozen and I'm really confused and don't know what to do. She has an older iPod (3rd generation, dock connector) that has given her some problems over the years but nothing like this. Unfortunately, she's traveling tomorrow and really wants her iPod and music with her. At this point, neither the Mac nor the PC will load the music onto the iPod. What do we do? Also, she has Applecare for her new Mac, but it looks like the issue is with the iPod, not the computer - if I call them will they help me fix it? Should I bother trying to bring the iPod and the Mac into the local store?

Now it gets even weirder.
I tried plugging the iPod into a third computer (PC) which belongs to someone else. The computer restores, syncs and loads all of his songs onto her iPod perfectly fine.
The only thing that makes sense is that there's somethng about one or more of her songs that's causing this problem. Is there anyway for me to find out which songs are doing this?

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