160 GB iPod Won't Sync All Songs From iTunes

I have a 160 GB iPod and barring the normal song-skipping issues everyone seems to have, I've had no problems out of it. That is until a couple of days ago. I would attempt to listen to a song and it would skip to the next one during the middle of it. It would run sluggishly, skip nearly every song, and at times, freeze. So I decided to exercise the restore option. After that, when I tried to sync it to my library, it only synced 330 (out of 14,000 plus)songs, all of them artists starting with A. I've tried rebooting and restoring the iPod to no avail. I even did a system restore for my entire computer. Nothing works; it insists on giving me only a fraction of my music library. Any suggestions?

*Hard Drive Diagnostics*
Take your iPod and place your right thumb on the centre SELECT button and your left on the top MENU button. Press down both thumbs for about 6 seconds until your iPod reboots. Immediately move your left thumb around to the rewind button |<< on the left and hold this down together with SELECT for a further 6 seconds. Your iPod should now switch into Diagnostic Boot mode. Press MENU for *Manual Test*, then select *IO > HardDrive > HDSMARTData* to reveal your stats. For comparison here are mine for my 2 year old 6th Generation Classic:
Retracts: 889
Reallocs: 12
Pending Sectors: 0
PowerOn Hours: 2202
Start/Stops: 894
Temp: Current 24c
Temp: Min 10c
Temp: Max 50c
Take a note of your results. When finished press *SELECT & MENU* for 6 seconds to reset the iPod again.
With modern disc drives sectors are no longer marked bad by a disc scan, if the SMART firmware detects a sector it has trouble accessing it will attempt to invisibly reallocate it to a spare area of the disc.
Note that I've only 12 remapped sectors and none pending. To help explain what the numbers mean here is an extract from the Wikipedia S.M.A.R.T. article:
*Reallocated Sectors Count*
Count of reallocated sectors. When the hard drive finds a read/write/verification error, it marks this sector as "reallocated" and transfers data to a special reserved area (spare area). This process is also known as remapping, and "reallocated" sectors are called remaps. This is why, on modern hard disks, "bad blocks" cannot be found while testing the surface – all bad blocks are hidden in reallocated sectors. However, as the number of reallocated sectors increases, the read/write speed tends to decrease. The raw value normally represents a count of the number of bad sectors that have been found and remapped. Thus, the higher the attribute value, the more sectors the drive has had to reallocate.
*Pending sector count*
Number of "unstable" sectors (waiting to be remapped, because of read errors). If an unstable sector is subsequently written or read successfully, this value is decreased and the sector is not remapped. Read errors on a sector will not remap the sector (since it might be readable later); instead, the drive firmware remembers that the sector needs to be remapped, and remaps it the next time it's written.
Large numbers of Reallocs or Pending Sectors would suggest your drive is failing and that you may need to repair or replace your iPod. Check your stats after another attempt to update your iPod. If the numbers increase that again points to hard drive failure. While it won't be good news at least you'll know it isn't some random software problem and you can decide what to do next.
tt2

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160 GB iPod Won't Sync All Songs From iTunes

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