Some songs sync and some don't....

I can get some of my songs to sync to my nano, but others don't and no error message pops up. I can sometimes get them to sync IF I add them to a playlist, but that shouldn't be required. There is no exclamation mark to let me know there is a problem locating the song and they play just fine as long as I have itunes open, but don't sync...I have enough memory, and I have my settings selected to where only checked songs sync and it is checked.....
I have turned on and off my computer, nano, internet, etc.....
Any advise....

I am having very similar issues, I purchased an album on my iPhone and it's not showing up on my iPad or Mac and I have iTunes Match plus it should auto update based on the fact it's all one account!!!
Mavericks and iTunes 11.1.2 problems I am sure!!

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