My iPod won't sync new music

This is a long explanation of my problem: I have an iPod Nano 6th gen that I've had for years with a pretty large playlist. I also just upgraded my iPhone to the 5s and have made recent music purchases. I just recently purchased a new laptop and am trying to sync the new music to my iPod. I can see my iPod being recognized in my iTunes, but I can't get any of the music to play (the text is a dim gray color), but the recent music purchases from my phone will in a separate playlist. I can't find a way to combine the 2 playlists and update all the music onto my iPod. How can I combine the 2 playlists, and sync them to my iPod? I tried going to the music settings on iTunes for the iPod, and it has "sync playlist" checked (once again, gray text and I can't change options). The only box I can check is the one at the top, but when I check it a warning window pops up and I'm pretty sure it's warning me that all the content on my iPod will be wiped clean. Help

That error means that yo are trying to sync more media to the iPod than you think,
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod        
Try syncing using the manual method

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    Drag the folder with the music into the open iTunes application window.
    (48009)

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