IPod keeps running into errors when syncing

I recently bought a classic from a friend (don't know if it's older classic or new-wave one) and whenever I connect it to my computer a message pops up saying there's an error with my device. When I try to sync, it loads anywhere from a couple to a couple hundred songs, then stops, often converting the music just put on into the "other" category rather than recognizing it as music. I've restored it countless times, tried using a different computer (that is also on a different operating system), checked for iTunes and iPod updates alike, enabled and disable disk use, and nothing seems to be helping. Is this iPod just toast, or is anyone else experiencing this?

Ok- I have found a few things. If you have XP make sure that you are running the SP2. You can do that by running automatic updates or by going to Start->Windows update on the scroll menu and install the latest Windows updates. If you do auto updates you should be cool. If you are running on anything less than XP or Vista (like 2000)- you are out of luck. You will need to upgrade to XP or Vista.
2nd option: http://docs.info.apple.com/article.html?artnum=304996
3rd option: One guy said he tried downloading Winamp 5.5, transferred all of his songs then for fun wanted to sync to iTunes to see what it would do. Low and behold it worked for him.
So far, I've done the 1st 2 and I am syncing now.....Seems there are some bugs with these. Hopefully in another update or 2 it will all be resolved.
AHHHH!!!! I just got error -53!!!!
I am officially discouraged. Apple for the love of God, please help and give hope. I would like for this to work. It's bad enough it will not work with the Philips DVD player without the AV cables. HELP!!!!!!!!!!

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