Abusive of that service! Hah! That's nowhere near the real abuse that's allowed to go on through relay service.
I've never heard of a hearing person getting probation for making harassing phone calls, so where's the functional equivalency? If you're going to punish her for abusing this service...
You don't use iTunes. Just plug in your Sidekick, and drag the files into your Sidekick's music folder using Windows Explorer. Simple drag and drop. No special software. Plus iTunes is only used for Apple products.