Any fix for random art and song order problems after adding new music?

If I sync my touch with itunes as a restore, all cover art, albums and playlists are correct. Once I add anything new or make a change and re-sync, random cover art is missing and random songs are in the wrong order. The only way to fix the problems is through a complete restore. Has anyone else had this problem or figured out a fix? I am using the latest itunes on a PC with XP.

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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