IPod stops syncing about 20/50gbs in, and makes unhealthy sounds.

Well, here's the story. I'm sorry in advance that it's such a huge post.
I haven't used my iPod classic for about 8 or so months now, and it's just been chillin in my drawer, turned off. Yesterday, I decided to plug it in to update it with all of the new music it's missed over the past 8 months. Once I plugged it in it froze for a bit, and iTunes said something was wrong with it, so it needed to be restored. Now, you should know, I've had this iPod since December 31, 2007. I have kept it in pristine condition, no scratches, marks, it basically looks brand new, and I've never dropped it.
So on to my actual issue: Once I started syncing the music, it basically got to approximately the 2500th track, and stopped syncing. When I would plug it in to sync the rest, iTunes would freeze, and I couldn't do anything until I just unplugged the iPod. Once I unplug the iPod, iTunes tells me that I don't have enough priviledges to access the disk, or something along those lines. Well, the issue was worse before, because before during this started my iPod just wouldn't respond and my system would hang and iTunes wouldn't force quit even though it said it did.
Now I restored it under Windows, and put it in manual mode, went to my Mac and same thing happens except this time..... all of my music that got on the iPod is now displayed as OTHER and it doesn't show up on the iPod. I think, maybe thats just a OS issue, since its restored under windows now. I restore it under OS X again. But this time it's more manageable because it doesn't try syncing automatically. Every time I have tried to sync it for the second time, it stops at the 13th-16th song and then I hear an unhealthy mechanism sound coming from the iPod. I've checked if it was a faulty wire, since I have 2, and both have the same problem. Also, when I plug it out after it pulls some of these shenanigans, it shows the OK to disconnect screen, and once the bar reaches the end the iPod resets itself, and makes some more strange sounds in the process.
Well, that's my story. I'm freaking out because I leave for Germany tomorrow, and now I won't even get to listen to my iPod on the plane.
Is there anything I can do? Are there any diagnostic tools I can use to tell if my iPod is dying or not? Any help would be sincerely appreciated. Obviously, my iPod isn't under warranty with Apple anymore, but I have a repair plan with RadioShack. It takes like 3 weeks though, so that's really out of the question in terms of action I can take right now.

Try to put your ipod into disk mode and run disk utiliy to see if there are any corrupt files on the HD.
http://support.apple.com/kb/HT1363
Reformating it and restoring it again would be another option.
Restoring: http://support.apple.com/kb/HT1339
Looking at the date, you might be on your plane already, good luck anyway

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IPod stops syncing about 20/50gbs in, and makes unhealthy sounds.

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