HT1420 Why won't the songs I have downloaded recently from Itunes store, load to my Ipod. Since I switched to Windows 8 I am having trouble. HELP!

Why won't the songs I have downloaded recently from Itunes store, load to my Ipod. Since I switched to Windows 8 I am having trouble. HELP!

What exactly happens when you try to sync?
Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
If so have you done anything like update iTunes on the computer since it last successfully synced?
Do the songs play in iTunes?          
Are any fo the unsyning songs DRM protected?
What is the detail format of the non-syncing songs?
Does any media now sync to the iPod?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod       
Try syncing using the manual method                
Managing content manually on iPhone, iPad, and iPod

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