My iPod loses songs every time I sync it
I'm a Zumba instructor and I change playlists almost every day. Every time I adjust my playlist in iTunes and plug in my iPod to sync it, random songs won't play. There is no consistency to which songs these are. I have to manually try to play each song in the playlist I want to play that night in order to check and make sure they will all play before I go to class. Usually it takes two or three syncs for all the songs to decide they are going to play. I was about to do a factory reset, but I wanted to see if anyone had any other ideas. This started when I installed iOS 9. :-( I have 9.0.2 on there and I've tried restarting iTunes, iPod, and Mac. No luck.
iPod touch (5th generation), OS X Mavericks (10.9.5)