Tho I select a song to play, it won't play (true for most of my iPodsongs )

With my iPod Nano 5th gen, though I select a song to play, it gives me only a brief glimpse of the CD cover then the list of songs returns, it refuses to play the selected song, in fact most of my many songs, including iTunes purchased songs (except for the last two I purchased).
What is the problem here, is it software, and what is the fix? I tried 4 of the 5 R's, not quite ready to do a full "Restore" yet. Can anyone help me?
Also, though I have 9 GB of audio on my 16 GB Nano, and another 1 GB of Videos, yet it says I also have 11.6 GB of Free Space; Why does the Nano do this, and what is the fix?
Using latest iTunes in MS Vista; my iPod software version is up-to-date.

Also, though I have 9 GB of audio on my 16 GB Nano, and another 1 GB of Videos, yet it says I also have 11.6 GB of Free Space; Why does the Nano do this, and what is the fix?
Games & the other items that come pre-installed take up space.
I tried 4 of the 5 R's, not quite ready to do a full "Restore" yet.
Try resetting your iPod. Directions for doing so are in the iPod Nano 5th Gen. User Manual (direct PDF download)

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