You don't have $8 a month? Cause that's all I'm paying.
I run things on an elderly PC through an internet connection here at my house. So long as my son, the gamer, isn't home from college, things run pretty smooth.
The automation program I like is Zara Radio
which is free and has been working rock-solid in my attic studio for 3 years. Though I am thinking of switching to using one of my Macs and using Radiologik
For the casting, I use the Shoutcast plugin in Winamp. Oh, and that $8 I mentioned goes to Streamgeeks
who are pretty good. Mostly, I ended up paying for a server because I could never find a path through my firewalls and whatnot.
Be patient, it does take a lot of time to get a streaming station working correctly. Write me if you like.