Cant sync songs- numerous errors and issues- anyone up for a challenge?

Question

okay so first a bit of backstory
So about a month ago i downloaded the new itunes (10) for windows.
It could have been connected to it and could not have been, but my 160GB ipod classic started going funny. it will skip songs halfway when playing them, and not play other songs.
So i decided to try and restore it, going by the book. so i first took out all of my extra stuff i had on it (I have been using it as a storage hard drive for pictures and movies round 10gigs) and restored it.
However, when i tried to resync it with itunes, it would only sync to about half way through, and say Itunes could not sync (name of song) to the ipod (ipod name) because the file cannot be read or written. alternatively, because an unknown error has occured (-50). so i will only have about half the songs (usually less) on my ipod or non at all.
I tried these solutions :
http://support.apple.com/kb/TS1539 and tried resetting the ipod, restoring the ipod several times and reinstalling itunes but non helped.
all i got was more problems, such as sometimes when i plug it ,my computer will also pop up with a message saying "windows was unable to save all the dad for the file F:, the data has been lost. this error may be caused by a failure of your computer hardware or network connection. please try to save this file elsewhere"
and "The specified I/O operation on \Device\harddisk1\DR9\ was not completed before the time out period expired.", together with the old ones.
also comes up "The Ipod (name of ipod) could not be synced. a duplicate filename was specified" and a few other varieties of these messages.
so evil ipod 1 itunes support 0
would anyone like to take the challenge of trying to help me????

Answer 1

While you may have got away with skipping the disk checks for some time it is there for a reason. iTunes may well decline/be unable to properly restore a disk which is in an inconsistent state. Have you yet checked via diagnostics mode (see link my earlier post to this thread) to see what the SMART stats are for your drive?
To check your disk for consistency connect your iPod and open a command prompt (Start > Run > CMD) and enter ChkDsk X: /R where X is the drive letter of the iPod. (If it doesn't have one disconnect, stick it in disk mode and reconnect) This will perform a full scan of the drive which attempts to read & write to every sector. Depending on how the drive & the operating syetem handle things it may that no "bad" sectors will be detected during the scan, but any that can't be reliably accessed should be added to the "pending sector" count. Following the disk scan you should again check the stats (see earlier link) to see where things stand. Restoring the iPod via iTunes should release the pending sectors so they can be taken out of service and become reallocated sectors.
With luck there is a fixed number of problem sectors and once these are mapped out your iPod will behave normally. Worst case is that the drive is deteriorating with use which would be apparent if repeated attempts to restore and populate the drive leads to increasing values of pending & reallocated sectors.
tt2