1) use usb. He wants to be able to "use the usb capabilities" of the iPhone. I can get more details if you'd like.
2) Use a music app other than iTunes. It irritates him and from the little I've used it I feel the same way. The only reason I've used it is to purchase songs I couldn't find anywhere else. Like Speck!
Please let me know if you can help either through personal experience or through resources.