I was looking at all the CDs I've been ripping and have decided on a new project I want to try. I want to set up some kind of streaming server that randomly grabs music from my playlist and broadcasts it. Then I want to make a simple web interface so that I can 'request' songs. So while it's random I can just request a song and it will show up within the next 30 min, kind of like a custom radio station.
Of course the next thing to do would be to find a way to share this with friends. You could share bandwidth costs with a few people and only let those people in. And only give those people access to the web server for requests. Have everyone contribute music to it so that you have a nice big collection of stuff. It would also have the bonus of exposing everyone to things they may not have heard of before. The thing I wouldn't want to do is just have it open to anyone. Once you do that things like bandwidth cost becomes a much bigger issue.
As I think about this I'm realizing that there are all kinds of wacky things you could do. You could have it so that people could give a song a thumbs down, and if 80% of the users give it a thumbs down it doesn't get played (and the thumbs down time out after like a month).