Over the last year I've done a few workshops for folks on Windows and I can tell you that you are spot on with your dicision to use 1.8.7 for now. It's so much more stable on Windows. The target audience for this package doesn't understand the various nuances that exist with Ruby, and really just expects things to work. With 1.9.2, I can get a newbie through an introductory class and tutorial, but as soon as they go outside and try to follow a RailsCast with a newer library, stuff starts getting weird.

I hope that this increases visibility on Windows so that gem maintainers will pay more attention to that audience when developing and improving their libraries.