
I own an AirPort Express wireless access point that I used to stream my iTunes music to, so that it would play on the stereo equipment. In my current home though, my stereo sits in a corner, where an airport unit would cover my room but never the whole apartment. Also, I would have to pull an ethernet cable into my room for wireless internet access. So I put the airport unit into the hall instead.
Before the App Store launched, I used to run a simple web service on my notebook. Written in Python, it would report the currently playing iTunes track using Python — AppleScript bindings. The iPhone would load a page containing an iframe for the actual audio resource (the HTML 5 audio support is not yet available on the iPhone) and an poll for song updates via XMLHttpRequest. This solution worked so-so, as there was a pause between tracks because the iPhone browser had to bring up the Quicktime plugin in a slow animation for each track, before even preloading the actual song file.
Fortunately, Julien-Pierre Avérous offers his web radio streaming client FStream at the App Store for free! What's left to do now, is turning iTunes into a web radio station using free components: