Ipod not syncing correctly and songs skipping on ipod but not itunes/wmp

My old ipod was having this same issue(so I presumed it was broken) and I wanted to get a new one as the old one was an 8 gig and didnt really have enough size for me so I bought a new 32 gig ipod. Unfortunately this new one is having the exact same problem and I cannot figure out why. I've tried uninstalling itunes and all the other apple programs and reinstalled them all and I've tried converting the songs to AAC but these have had no effect.
The songs play perfectly in both itunes and windows media player it's just when they transfer over to the ipod the problems start. Usually what happens is the song plays for xx seconds then the sound stops but the song continues playing on the ipod if I leave it alone the ipod skips to the next song but if I force it to speed up eventually the song kicks in again but at a different point. Other times the song will play out of sequence and will sound completely disjointed.
Another problem that keeps cropping is when trying to sync the ipod it will get about half way and randomly cut out on one song telling me it's corrupt but it's always a different song and will happily skip over previous songs that caused a problem when I run it again.
I would import all the music again but I don't have access to the CDs as I am out of the country for a year, I didn't buy any of the songs through itunes so can't re-download them either.
I am running vista 64 bit but I used the 64 bit installer so I'm not sure if that would really cause any problems or not and yes I made sure the ipod is up to date and I have tried resetting it numerous times.

It's hard to say without a lot more information; Here's a sample of things that would need to be answered in order to really determine the cause:
*Age of the computer and/or hard drive
*What application(s) are installed
What updates occurred or new applications were installed before the issues started popping up
*Whether files/folders have been deleted
About the only one that really matters for you now is the age of your hard drive. Most hard drives last for 3~5 years, and the hard drives on the newest iBooks (from 2005) would be nearing that 4-year mark. If you've never had your hard drive replaced, there is the possibility that the hard drive is failing. Hard drive failures can result in software corruption--which would be the issues you're seeing.
What you want to do from now on is make sure you have all your important data backed up (and all installation CDs/DVDs accounted for, just in case) and monitor the machine. If the odd behaviors return, we may have to do more troubleshooting.
Good luck!
~Lyssa

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