IPod Classic not syncing past say ~500 songs, -50, -69, -1404 etc.

OK So I have the Ipod Classic 120GB model. I've had issues with it before, mainly after the first time I accidentally took the iPod out when it wasn't done syncing. Anyway the 2 or 3 times my library got wiped I was able to get it back (process of finding which songs were causing the sync to fail and reformatting iPod)
Anyway, a few weeks ago I was trying to give my brother some of my songs and I had used a program for my older ipod (a 5G Ipod Video 30GB) I'd used successfully in the past to copy the library to my computer called CopyTrans or something like that.
I tried it with the 6G and it got halfway done then the iPod froze or just failed, my brother got no songs on his computer (running XP) and my iPod got wiped. I wasn't mad since I figured I'd just restore it (running iTunes 10 on Windows 7).
It's been about a month and I have not been able to get my whole library on my iPod. I've tried reformatting under every setting, numerous restores, trying different iPod USB cables (for some reason my older one with the side release buttons works better at times, the others sync to fast and just freeze and fail sometimes).
My iPod will begin syncing usually fine, until it gets around ~500 songs or gets to certain songs then it will display Connected and just sit there (on iTunes 8-9 the whole iTunes would just freeze) iTunes 10 seems to keep running and the iPod section just freezes and for not as long, it usually comes back within 3-4 min, but with error codes and not syncing everything I asked it too.
I've even tried unchecking and converting the songs that mess up (Create an MP3/AAC version) which seemed to be working at first but now is not and I have numerous copies of songs in my Lib.
Any help is appreciated? Should I take it to an Apple Store? Is there any other methods to try or is my HD pretty much shot.

*Check your iPod with Diagnostics Mode*
It's possible that your iPod's hard drive has started to fail. 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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