SYNCING PROBLEM 1309 IN A MAC, Ive tried everything on the site it doesn't work.

Ipod Nano 6th generation:
Ive had this product for a little over a year (it was a gift for christmas 2010) ive taken care of it really well and it has been used properly without problems until november 2011. I restored it but the issue continues to persist Ive been able only to add about 250 songs when I used to have over 2,000. The pop up warning continues to appear so I cant add any more songs to my ipod. Im trying to find a solution to this problem, Ive tried doing many of the things on the site but they dont work, I dont believe apple has placed really good answers just dumb solutions, that dont work.
Before anyone says anything on to updating. EVERYTHING IS UP TO DATE. I use Lion on my macbook and my iphone 4 s didnt have any problems in syncing music.
I dont go to the mac stores because I live in El Salvador and I dont trust those technitians, I believe theyll over charge me, so I prefer solving the problem myself.
Im thankful for any answers you may give me.
Kind Regards,

http://support.apple.com/kb/TS2830

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Hi Baileyfour,
Welcome to the Support Communities!
The articles below may be able to help you with this issue.
Click on the link to see more details and screenshots.
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http://support.apple.com/kb/TS1630
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http://support.apple.com/kb/ht3576
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http://manuals.info.apple.com/en_US/iphone_user_guide.pdf
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