Be aware that as of the last time I read the license agreement, the suggestion to use Skype in this manner is a violation of their terms of service unless you give them on-air credit every 15 minutes.
If the Barix Exstreamer will reconnect with a WME stream, that solutions seems like a no-brainer. The Exstreamer is inexpensive, particularly if you don't have to buy the Instreamer to go with it.
Partial thread hijack: Last weekend, I played around with streaming audio using Adobe Flash Media Live Encoder (FMLE), a free utility. I was able to create a high bitrate MP3 stream in stereo on Ustream that was excellent quality. The separation, even for MP3, was amazing. You can stream without FMLE, but the quality is higher with it.