Something is screwy with my itunes setup... I can play multiple songs after each other from the Music Library, but if I want to play several songs in a row from a playlist, it doesn't seem to work. It plays one and then stops. Any suggestions?
ARGH -- never mind, I figured it out -- you have to have songs checked; it only plays the checked songs automatically, and skips the unchecked songs.
I wish iTunes handled some of these things a little more intuitively or at least gave you feedback if you're not doing things the way it likes.