"Both things have the same problem: I can only run one iTunes instance on a particular machine, and iTunes has to run under a real login account, not something like nobody, root, or some other bogus user I make up. This makes some sense, but it is still annoying to this unix guy."

To me this is a serious limitation -- I want to have multiple concurrent users accessing my site and playing different songs/playlists.

I have this partially working with an app I am writing in ColdFusion MX. (Coldfusion programs compile to Java byte code, so performance is similar to a Java program serving these files.

The progam parses the iTunes Library.XML and builds a memory-resident structure of tracks and playlists -- this structure is cached until the iTunes library is changed.

Users access the site (login optional) and see the playlist/songs much the same as it is displayed in iTunes and WebRemote.

When the user selects a song, that song file is located and "played". iTunes does not participate in any way and need not be running.

Different users can play different songs -- concurrently.

This is just a web app that serves song files instead of information from a db -- it just builds on what iTunes has already done to organize the trank/playlist info.

Dick