Blog from the Maker of Joobik Player - iTunes Video Playlists on iPhone and iPad.
Blogs about Objective-C and iOS, Software Development,
Tips and Tricks around Apple Devices, and Hard- and Software.
To solve this problem, I would like to suggest you an amazing product called PlayerXtreme. It has an auto sync option by which all your media files will be synchronized with the app once it is activated. It never skips a track and it also has options like shuffle play, repeat play, repeat play once, repeats play forever. Try It.