Songs don't show up on iTunes

When I synced my nano to my macbook, it showed up that there weren't any songs at all though my playlists were intact. I also checked how much memory was left, and my 16gb nano was pretty much full. I thought it was just being difficult, so I restored my nano to factory settings, but when I tried to re-update my nano (with some in specific playlists, and some songs just added) it still showed up with NOTHING in my music list. I added around 2gb of music so far. When it's not connected to the computer, it seems to show the music just fine. However, if I were to remove and add music, I need to be able to see my comprehensive music list!
I have an iPhone with the latest software, and it doesn't seem to be having the same problem. I noticed when I synced it, it was a little slow in updating some apps (I deleted some and added some), but found there were no faults when I toyed around with it.
I run with my iPod, so does anyone have suggestions?
Thanks so much!

Are you selecting the playlist like this
Connect the iPad to the PC and launch iTunes.
Click on the iPad name on the left side under devices.
Click on the Music Tab on the right.
Click on all of the albums or playlists that you want to sync
Click on the Sync Music Heading.
Click on Apply in the lower right corner of iTunes

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