Thanks for all the replies so far!
I really am loving the advice AND concerns that you have brought up. I know this may seem like a foolish venture, but I am fairly set (already have over 200 supporters), and the movement is building. So please keep the comments suggestions, and warnings coming.

Here's a pertinent question: BESIDES the winter weather, what kind of risks does my body entail from riding like this?
Any suggestions for how I should train for the next 3 weeks?