IPod problems that keep getting worse...

Question

There isn't really a specific title that can fit my current dilemmas with regards to my iPod classic as there are many issues that I am currently pulling my hair out over and am in desperate need of getting my iPod back on the road.
Firstly a little background information as this may be part of the cause. I have had my iPod classic since the end of January this year, so it's not very old. My computer I am currently using however, is about 4 years old so is quite slow and battered. It does work though, and with relation to my iPod there is only one cause for concern. Whenever I plug my iPod in or any USB device that is, after a while the computer completely freezes up and the only way of resurrecting it is rebooting it. I don't know if this is related to my other problems, but this may be of use in diagnosis.
Anyway, about a month ago for some reason when trying to manually (I don't automatically sync my iPod) add an album, my iPod just seemed to flip out and the error 'Delayed Write Failed' came up. On ejecting my iPod all my 5000 songs and everything else had been wiped. After researching this problem on the internet I tried a thing called Disc Caching "Because iTunes tries to push as much data as possible as quickly as possible, Windows was unable to keep up, resulting in the error." this seemed to fit my problem, like I said the computer was old and this sounded about right. Unlucky for me, it wasn't that easy and I had no joy.
I've lost count of the amount of times I restored it and every time I try to add new music the same 'Delayed Write Failed' message comes up, or the computer just completely freezes before the message has the chance to come up. The message usually appears after putting 200 or so (there is a definite number of which I'm not sure of) songs on. I've also had the message 'attempting to copy to the disc 'iPod' failed. The disc could not be read or written to.' one or twice also.
This evening I tried again to get my iPod working, but it didn't even load up in iTunes (the programme opened, but that's as far as it got) and then resulted in a freeze up of the computer.
I shall try my iPod on another computer to see whether it is the compueter's fault or my iPod itself, as perhaps this may shed some light on the situation. For the record I also have an iPod mini that I use to run with, this has always been fine and is working now as well as it ever has. I also tried connecting my classic with a Firewire cable which worked fine on the mini and didn't result in a freeze up either, but of course this doesn't work with the classic (I do know why).
I would appreciate some advice on my situation immensely as I can't live without my iPod and I miss it so much. Any advice I thank in advance!

Answer 1

I'm getting a new laptop for my birthday in about a week, so there's no need to reinstall Windows all over again. Plus I would probably make the computer blow up or something if I did this.
Tonight I tried my iPod on another friends computer. Although his is also old, it did not freeze up like mine. Now that is obviously a problem with my system and has already been addressed. However my iPod again proceeded to misbehave. It got to about 270 (ish) songs and then the dreaded error came up saying 'attempting to copy to the disc 'iPod' failed.' But when I ejected it, it still had the small amount of music that I was able to put on, on it.
Later, I tried to put about five songs on but the error: The iPod 'x' could not be synced. An unknown error occured (-1303).
So now I have diagnosed that it is obviously the problem with my iPod. Although, should I try it on my brand new laptop that may get rid of all the other previous problems?
I would be eternally grateful for any help as I can't stand life without my iPod!