Update on this! The build we posted last night has the Dragon Console in it, which keeps all the stdout text, so you don't need a separate terminal window anymore. In fact, using puts() inside your Ruby code will send it to the Dragon Console. Just hit tilde (or backtick...the standard "Quake console" key) to get at it. PageUp will scroll back through the text.
We think this solves the Windows problem pretty well.
Five-minute intro video to show you the Big Idea of the thing: