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Possibility 1)
use Windows Media Encoder and setup a live stream. This supports playlists and such. Does WMA and WMV streaming (audio/video).
alternatively use Helix Producer combined with Real One Player.
Possibility 2)
Mount folders on your PC drive on the PocketPC. There's some free tools available that allow you to do this. When you play content from that folder in any player software, the stuff is transmitted over WiFi. It's de facto streaming, even though your PocketPC thinks it's playing a local file.
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