Alright, think I've figured it out, dunno why I didn't notice this before. CF, as it was creating the song database or whatever it does, lists every single song twice. So I was hitting the back button, thinking it was just restarting the song over and over.
Breakdown -
Hit back button - started over song
hit it again - went to previous song in playlist, which was actually the same song
hit it again - started that song over
hit it again - when back to previous track
Guess I need to redo my music database thingy.

Yay for me!