try putting the "tracks" in a playlist in the order you want them played and drag the playlist to the device. experiment with that, and I think you will be able to predict the order as long as you don't enable shuffle mode on the ipod.

I'm not sure how to restart it from the beginning of the playlist. That depends on which one you have, I think, but you should be able to find the documentation for it on Apple's website.

-David