IPod Classic fails to sync after adding new music

Hi, so lately I've been having problems with my 160GB classic, I've always had problems with it but its gotten to the point where I am frustrated beyond belief. SO the problem arises when I add new music, it comes up with the error 'XXXX's iPod cannot be written or read'' and before it displays this message the sync usually sticks on a song, a random song that I would've added. I restored it a few times, scanned and fixed it a few times and then when I noticed I started skipping songs, some in mid-song I restored it again and the problem repeats itself. Help would be appreciated

A few issues, but sorry let me try to understand.
Adding new music, 'XXXX's iPod cannot be written or read'' can you let me know the number. most likely music format is not iPod Compatible like HE-AAC.
started skipping songs  - these are normally due to corrupted ID3 tags, try converting them -File-> Advance -> IPOD version or use MP3 validator to fix all songs in the library. (My Apologies, only work for MP3 music that skipped)
As for item 2, you can try Hard Reset if you like to download MP3 validator.
After charging till full charge, at least 2 hours (preferably 4 hours)
Toggle the Hold switch, make sure you dont see the red mark when you do the  next step
Reset the iPod -> Press Menu and Center button simultaneously for about 10 secs till the Apple Logo comes ON
Then release the buttons
Select your preferred language.
Here is the Apple support Article on the 5Rs
http://www.apple.com/support/ipod/five_rs/classic/
Good Luck!

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