You should be able to do the following:

1. Use DopplerRadio, a podcast/podcatching app, to subscribe to the C9 video feed. Assuming the feed is RSS 2.0 with enclosures, Doppler will check every x hours (I'd set it to once a day) for updates, and pull down any new videos.
2. Configure Doppler to add the new videos to Windows Media Player
3. Configure Windows Media Player to automatically sync the new videos to your Pocket PC (preferably to a memory card).

I've been meaning to set up something similar for a while. I've just been dropping the videos on my SD card manually and watching that way (I also do this with TV shows that I've configured my BitTorrent client to download automatcially). Once I work something out, I'll write it up and post it here to share with the Channel 9 community.

Josh