(Sorry, your message was stuck in a queue; the google group UI is tricky.)
It does sound like a challenge indeed :)
One of the main places that would pose problems is Babushka::Shell, which does a fork/exec combo to hook up pipes to the subprocess. I don't know how that would be done on Windows, or if it's possible.
Also, I should be upfront and say that I'm against merging significant patches for Windows support. Fixes are of course welcomed, and if Windows-specific stuff can be contained, then it might work. But I'm concerned about the maintenance overhead of code that I don't understand, and my inability to fix bugs reported against it.
Cheers,
Ben