My iPod and iTunes seem to hate each other

Question

They're just not hitting it off. They don't like talking to each other, both seem prone to going into long electronic sulks, and chucking crockery at each other can only be round the corner.
Ok, serious head on for full story. Short version: iTunes 7 won't sync with our 4th generation iPod. Sometimes it won't sync at all. Other times it'll get to a certain point and gets stuck on a particular song, and Force Quitting iTunes is the only way we can eject it safely so none of the songs end up on the iPod. Very frustrating when you've got up to 941 out of 5000 plus songs. Along the way we've tried the five Rs, had various unknown error messages (1428 seems to be a favourite), and had the folder + ! sign (now gone again).
The long version: Got a new car stereo that's iPod compatible right out of the box, and we felt that having our entire music collection on tap was more appealing than faffing around with a CD changer. The Mac we bought a few months ago had iTunes 6, and other than locking up a few times it was happy to import 300+ CDs. So far, so good.
Next step, we got a second hand iPod, and this is where the aggro started. It's a 4th Gen 60GB model, and we immediately ran into difficulties because it had been used with a Windows PC. iTunes 6 didn't want to know, so looked online and found we needed to update to iTunes 7. Did that, only to find we then needed to update OSX as well. At this point I started getting all misty eyed and nostalgic for the old Windows PC - I mean I've still got ancient Win95 stuff that worked ok on Win2K. I really didn't expect this much aggro when we switched to Mac. Anyhoo, did the OSX update (which took days since there's no broadband available where we live), and finally we could get the iPod plugged in. Needed to do a restore on the drive, but that went smoothly. Then we went out and left it syncing.
Sinking more like. It got stuck on the 941st song not long after we got home, and while we were looking we got an error message saying we'd disconnected it without ejecting first. We hadn't touched the iPod, which was still sat in is dock, but as far as it was concerned it had been pulled out. Which meant that we needed to restore it. Again. Which it didn't want to do. After many attempts we found that forcing it into disc mode allowed us to restore it properly. Then tried to sync again, but only with one album to kick off with. That worked ok, so we tried another 2 albums. Got stuck again halfway through the second, but we were able to eject it semi-properly so that resetting worked. At this rate 20+GB of music is going to take so long to get through that our furniture will be antiques before we're done. Nnnnnnnnnnn.
Next attempt got to just over 800 songs synced before it got stuck again. This time it left the Mac completely unresponsive, which meant another restore. After that I went beck to trying one album at a time. One went on okay, the next stuck on the first song. At this point we've given up trying to suss it out ourselves and have come here for help. Is it worth trying iTunes 6 again? 7 has locked up the computer when the iPod wasn't even in the dock, and although this happened a couple of times when we were importing CDs into iTunes 6 I wonder if the older version might be more stable. What else can we try that we haven't had a go at already?
Thanks in advance for any advice offered.
Mac G5   Mac OS X (10.4.10)   Old Win2K PC in the back room

Answer 1

Hi Michael!
Just wondering if you managed to resolve the issue? i'm suffering from the exact same problems-my shuffle works on everyone else's computer but not my notebook, which is new as well. everything is fine until i try to add songs then it just freezes. After a while it says cannot read from or write to disk. if i try to restore it, it takes hours or says there is an error. i have literally tried everything and even been sent a new one from apple. it's driving me crazy. please help anyone!
Matt