What to choose
Streaming technology evaluation
Both streaming technologies (Windows Media and Shoutcast/Icecast) are excellent solutions and they both have positive and negative aspects to them. Generally though, Shoutcast streaming is considered as a better value for money option, since in large scale broadcasts it uses the MP3 codec, which is a lower sound quality, while Windows Media are regarded as a more professional solution, for broadcasters who demand high quality even on low bitrates.

Encoding technologies Windows Media Eco ShoutcastEco Icecast
Primary audio codec WMA MP3
Good quality on low kbps (up to 48kbps) Yes!  
Realtime statistics Yes! EXCLUSIVE Yes!
Windows Media Player reproduction Yes! Yes!
WinAmp reproduction Yes! Yes!
Fast Start - Listeners don't wait Yes!  
Professional Advertising Opportunities Yes!  
Web-based player Yes! Yes!
Flash player   Yes!
iPhone/iPad support   Yes!
AutoDJ service   Yes!

Formats comparative table
Τhe aacPlus format is the undisputed winner as far as sound quality is concerned, ideal for online streaming and for reproduction on portable devices.

Unfortunately though, its limited support by players leads us to widely use Windows Media as an absolutely decent solution.

You can also turn to Wikipedia for more extensive information on audio codecs.

  Eco Shoutcast Windows Media
Audio Yes! Yes! Yes! Yes!
Video     Yes! Yes!
Live Streaming Yes! Yes! Yes! Yes!
On-Demand Streaming Media Yes! Yes! Yes! Yes!
Windows Media 11   Yes! Yes!  
Windows Media 12 Yes! Yes! Yes!  
WinAmp 6+ Yes! Yes!    
iTunes   Yes!   Yes!
Real Player Yes! Yes! Yes!  
QuickTime Player   Yes!   Yes!


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The most common misunderstanding

The audio codec you use and its compatibility with players are two different things. Today all the modern players like the Windows Media Player and WinAmp support both WMA and MPEG reproduction.
Some specific advanced features, like Fast Start by Windows Media for example, are only supported by the WM Player, but this does not mean that the listener will not be able to listen to your station no matter what player they're using!!!!