Whats wrong with my ipod classic??

Maybe someone can help me with my iPod classic 160 GB...
I have over 25,000 songs in my itunes. I have tried everything: Syncing entire music library, syncing half of it, then syncing in batches of 10GB. I always have the same problem at around 32 or 33 GBs it gives me an error message sayin smething like: cannot sync song "Whatever" error (50).
I have restored ipod many times, used different usb ports, read every post on this and other sites. It is always the same it won't sync more than 30something GBs!!!
Please help because this TOTALLY bites. I only use my iPod for music. I need my jams. Just updated to 11.1.4. ITunes.
iPod classic, Windows 7
ANY advice would be appreciated.
Bison

Sounds like a hardrive problems. It seem to be the main problem with
most of the issues that have come up.
I myself am struggling with my ipod Classic.
And everywhere I look to figure out what the situation is,
points to the hardrive. Looks like the best thing would be
To replace it...
Apple likes to stick time stamped parts
that way it works for a while, then craps out
when you least expect it...
Good luck man.

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Use the USB2.0 port (at the back of the desktop, if you are not using a notebook)
Do not use any USB Hub.
Antivirus or other plugins conflict with iTunes - Stop the Antivirus and plugins,
Disconnect from Internet, as malware and other broswer plugins interferes with the Sync.
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- Try cleaning out/blowing out the headphone jack. Try inserting/removing the plug a dozen times or so.
Try the following to rule out a software problem
- Reset the iPod. Nothing will be lost
Reset iPod touch: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Reset all settings
Go to Settings > General > Reset and tap Reset All Settings.
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- Restore from backup
- Restore to factory settings/new iPod.
- Make an appointment at the Genius Bar of an Apple store. Seems you have a bad headphone jack.
Apple Retail Store - Genius Bar
Apple will exchange your iPod for a refurbished one for this price. They do not fix yours.
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A third-party place like the following will replace the jack for less. Google for more.
iPhone Repair, Service & Parts: iPod Touch, iPad, MacBook Pro Screens
Replace the jack yourself
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Whats wrong with my ipod classic??

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