My 4th gen ipod touch wont sync only check marked songs, how do i fix that?

I just got a 4th gen. ipod touch. it works fine everything is great on it but when i try to sync only check marked songs onto it from itunes it wont sync any songs at all. I thought i solved the problem when i clicked "autofill" in the music tab under "my devices" but all that did was randomly put songs on my ipod. i went to the settings and unchecked "choose items randomly" and tried again but it did the same thing. i know its not my computer cuz the same thing was happening with my old ipod. i have "sync only checked songs" marked but it just wont work. PLEASE HELP ME!!

http://support.apple.com/kb/ts1567
Basic troubleshooting steps
17" 2.2GHz i7 Quad-Core MacBook Pro  8G RAM  750G HD + OCZ Vertex 3 SSD Boot HD 
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http://support.apple.com/kb/TS1369
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HELP
Help needed to update a 4th gen ipod touch running version 4.3.5 (8L1) to the latest 6.0 version. When I connect and try to update i keep getting a box which states that a connection error occured and I cannot update.
I have been given a new laptop for xmas which runs on windows 8, and the new itunes version (which is in itself a hurdle as I am a technophobe!) and this is all becoming a bit fustrating.
I have connected, updated and synced my iphone successfully, but just hit a brick wall on the ipod. (which incidentally maybe where this laptop will end up!!)
Help if you can, but in laymans terms.......

Thank you for you input so far.....
I think we are getting nearer to the solution sort of!
Let me get this straight...... I have paid for content on itunes, bought the apple devicds in order to play said content, now I have to subscribe $25 for the privilage of playing MY library content on MY other devices. Which wasn't such an issue to do before the new and improved itunes version!!
Have I got that correct. I think I cannot associate my other iOS devices with my library because I am unwilling to pay further through the nose!!!??? or am I missing something?
Thanks
Frustrated even more now!!

My 4th gen ipod touch wont sync only check marked songs, how do i fix that?

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