Josh Mika is working on the iPodject at Beebe Elementary School in Illinois. Besides having a cool name, there are other cool things from the project. There's a website, blog, and wiki. These resources are all about using iPod classics in classrooms.
The wiki has a page devoted to listing schools that are using iPods. The list can be a good thing to show school administrators that your idea to bring iPods into the classroom isn't a crazy one.
The wiki also has several videos about iPods. Josh recently made his own iPods in Education presentation video. The video gives a thorough introduction to what iPod classics can do. I like the point made at the end: Would you like to learn, purchase, carry, move, and store a television, CD player, tape recorder, CDs, documents, and file folders or a single iPod.