Hello timnpaige,
Thank you for the details of the two issues you are experiencing with your iPod nano. For issues like this, I recommend resyncing the music to your iPod.
If you are syncing automatically, resync content to the iPod by unchecking "Sync Music" and clicking "Apply," then checking "Sync Music" and clicking "Apply" again.
You can find the syncing steps in the following articles:
iTunes 11 for Windows: Set up syncing for iPod, iPhone, or iPad
http://support.apple.com/kb/PH12313
iTunes 11 for Mac: Set up syncing for iPod, iPhone, or iPad
http://support.apple.com/kb/PH12113
If songs are still not playing in the correct order, I recommend reviewing this article next:
Troubleshooting songs that skip
http://support.apple.com/kb/TS3217
Thank you for posting in the Apple Support Communities.
Best,
Sheila M.