It's all about Community
Here's an idea, for UserLand or Live365.com. A really expensive one, but I think a good one.
What if UserLand did the same thing with Radio UserLand as they did with Manila?
With Manila, UserLand set up EditThisPage.com, and had a goal to see a million web sites blossom.
For Radio UserLand, they could set up something like Live365.com, but something that was totally integrated with Radio UserLand, controlled by XML-RPC or SOAP, so it was still open and accessible from other platforms. Let a million radio stations blossom.
Update: Duh, don't bother -- just integrate the FEATURES of Live365.com into EditThisPage. Make it a service that an editthispage site has to offer its readers.
Problem is: Expensive Expensive Expensive -- bandwidth and storage costs would be huge.
Why would I want this? Well, Live365.com has a couple of options. One is Live Broadcast -- that's the SHOUTcast option. You need your computer on and running WinAmp 24/7. The advantage is you can control your playlist and do cool things like DJ'ing with a microphone, etc.
But there is a really compelling option, EasyCast, in which you upload your MP3s, and Live365.com plays them. It's compelling because it requires little resources on the DJ's computer. It doesn't have to be on 24/7. Of course, EasyCast has a downside too -- it would take a while (and again huge backend costs) to transfer your music archive to make it available for broadcasting by the service. However, the biggest problem, IMHO, is you have to use their web site/application to change your playlist. There is no way to change it programmatically. It's not scriptable.
Now, take EasyCast, and put an XML-RPC or SOAP interface on it that Radio UserLand and compatible playlist generators can easily hook into. This would be easy for Live365.com to do, since they've already got the infrastructure in place.
I guess I want my cake and to eat it too. Dreaming...