I use a package called OnSong with my iPad2 which can also put out lyrics to the screen if you want; shows the chords and lyrics of course, and allows you to create "sets". You can also auto-pull back chords and lyrics from the web if you need a particular song. iTunes is useless.
This package was created mainly for people playing in churches I think, and so created specifically for playing your backing tracks.
It also always cues at 0 and and you have the option to stop and when it starts it starts automatically from 0 which is good.
Loads of other stuff.
The only thing I wish it included was EQ for individual songs, which would really polish it off, I've written to them about that.
Here is a link
http://www.onsongapp.com/perform/It also can be used with a foot pedal for starting and stopping songs which seems cool.
Cheers
Greg