I've been doing a theme park gig. Medium sized pa, I-pod and sax with wirless mic.
BB or pro-tracks makes it easy to make a file that I-tunes turns into its own file.
I-tunes is free for any computer. The only problem an I-pod, is that it will continue to play when your finished with the current song. So you have to be near your player when the song ends.
An I-pod will normally hold more songs than you'll ever use.EM

Eddie Marshall
Bands & woodwinds
www.orlandojazzmusic.com