This (iTunes/iPod) is actually a legitimate topic for the Travel Technology forum -- not sure why you started this thread in OMNI.
In fact, a "Search this forum" reveals that there are quite a few threads in Travel Technology with "iTunes" in the title, and even more with "iPod" in the title. I bet if you spent some time perusing some of those threads, you could learn some useful stuff.
Of course I realize you've already figured out your current problem -- but still, might be something helpful over in TT as well.