I have a -69 error, and my iPod is practically broken. HELP!

I have a list of problems:
-Only my left speaker works no matter what headphones I put in my iPod.
-I get an error (-69) when I try to update my iPod. The so called "corrupted file" is different every time.
-Half the songs on my iPod stop half-way and force a restart on my iPod.
I have done the suggested things to fix this problem.
PLEASE HELP!

try a safe boot & a normal boot. if it only works in safe boot, there is a software fix.
Shutdown your machine. Hold down the shift key. Poweron. Wait awhile Wait awhile while you harddrive
is being checked.
http://support.apple.com/kb/ht1455

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