Zara Radio and Broadwave Streamer, two tastes that go good together.

Zara Radio main window.
Zara

 I play a playlist that will go for a month then either repeat or shuffle and restart. I could do this with any audio player but the goal is to imitate a radio station by breaking up the list and injecting some radio station like breaks and play favorites more often.  I think in Real Radio the tool for charting the hourly schedule is called a clock wheel. I schedule the programming with several folders of source material :

Scheduling the breaks is in the Zara events settings. After several experiments I settled on Hotbox items twice an hour, station ID wisecracks twice an hour, comedy items once an hour and bits 3 times an hour. More than just playing all 10,000 of my favorite mp3s, it gives a radio station flow to the programming.

Zara can also add time & weather announcements if one wants more "Real Radio" emulation. 

Special events can be programmed too. Five O'clock on Fridays plays an hour of songs related to working for a living for instance.

Broadwave option panel. Really simple to configure and test. There's a local network access and a public (The Internet) access option.
Settings

Broadwave Input. This is what will stream. Could be the audio input and fed from a music player (simple) or mixer/processor/equalizer (not simple). Mine picks up whatever audio is playing in the computer's sound mixer.
Settings

 

Broadwave running and streaming live. Click on the Connect icon and it will bring up an html page with urls and a flash player to access your stream.
Broadwave

Sorry, I don't publish the url. This is meant for personal use.