ITunes 9.1 on early 2009 mini w/160gb ipod classic can't sync

Question

Having all kinds of problems syncing from iTunes to the iPod. At first I was getting the error saying it couldn't read or write to the iPod. Now it's saying unknown error (-50).
Went to Apple store yesterday. Guy there said Their solution? Delete itunes and download and reinstall. So I did. No change in problem. Now they want me to bring my ipod AND my mac into the store (at least it's a mini).
This is ridiculous and utterly unacceptable! Especially if this turns out to be the result of Apple's screwing with Palm as was suggested on another thread.
I'm going to try an old version of iTunes, I found 8.2 for mac and will see if that fixes things.

Answer 1

Have wasted untold hours since Friday on this. Am totally disgusted right now!
Have been trying to sync my itunes library with my ipod. Hasn't been synced for a while so there are a lot of things to update. That failed, so I restored to original (downloading and updating the firmware, wiping the ipod to factory and starting over) and it still failed.
Have moved files from the external hard drive to the internal hard drive (this is a mac mini). Still fails.
Tried a powered USB hub - still fails.
Tried manually copying files to the ipod - still fails, though because it's manual I am able to more easily control what gets copied, when, etc. and recovering a little less painful, but it's all manual at that point, and it still regularly times out with errors.
Tried iTunes 8.2 - still fails.
Yesterday I visited the Apple store and the guy said my ipod classic was pristine, and not making any abnormal noises or indicating any other signs of problems. He said to drag the iTunes app to the trash and download and reinstall iTunes. Still fails.
He said the only thing left would be to bring my Mac in and make another appointment. So after spending the entire morning trying to get this to work I finally begrudgingly make an appointment for when I thought I'd be able to come in. And then started a backup (clone) of my drive (just to be safe!). As it grew time to leave, the backup was still running, so I rescheduled the appointment.
The backup was STILL going, so I rescheduled again. And of course it was STILL going, so I tried yet again! The concierge page said 2:20, 2:40, 2:50, (4-6 times in the afternoon and 9 in the evening, for iPod visits) were available. I selected what I thought was reasonable (about an hour 20 minutes later - because now I had to come up with lunch for my daughter, I had planned on stopping on the way in to the store) and was told I was not allowed to have any more times today.
No worries, I figured I'd call the store directly. After sitting on hold for who knows how long (no big deal, at least it told me how long I was in the queue and that was tolerable) the guy says there's no more times available today, they are all booked up. SO - they are all booked up? 13+ appointments all went poof in less than 10 minutes? On a Sunday? Really? I mean, maybe they did, but it sure seems odd given what I was seeing throughout the day.
All because the backup was taking longer than normal, no doubt because of all the futzing around I did trying to get things to work. Normally the backup takes about 45 minutes - it's been going 90 minutes now and is still going. And just so I could bring the computer in with the iPod so they could see "Yup, it's not working!" I don't know what I expected - I seriously doubt they could do anything I've not already tried.
There are only two possible issues that I have not been able to isolate - the mac mini itself or the cable I'm using. That's why I was even willing to go through all this hassle and go to the store.
Fortunately 90%+ of my library are MP3s and not AAC, so I'm not locked in (Amazon has some great specials on MP3 albums) - and to think, I had been planning on getting a 64gb ipod touch. Not any more!