Cannot add purchased songs to iPod

I am about ready to throw my Macbook out the window. I detest the new makeover on iTunes making me feel like a complete idiot that I cannot figure out for the life of me how to transfer one stinking song that I purchased on iTunes to my iPod Touch. I have confirmed the song is in my music library, I have synced my Ipod several times. I appreciate any help on this!

My problem is similar but broader.  At some point a few months ago, I could no longer listen to any of my purchased music on my iPod Touch.  All of the purchased music remained in my iPod music library (I can still see every song); however, none of my purchased music will play.  When my playlist reaches a purchased song, the iPod stops playing.  I've re-synced my iPod many times and the same thing occurs.  And, I've restored my iPod with the same end result. 
One other issue that I believe may be related: I'm also noticing that some of my playlists don't show up on my iPod anymore.  All of this seems to have occurred at the same time.  And I still have 22 GB of capacity available so that isn't the issue.  Can anyone offer a solution?  I would really appreciate it. 

Similar Messages

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