@dsmid: I like zenity as It's also implemented in python (sudo pip install pyzenity). I like the auto upload a log idea, I think Ubuntu's bootrepair disc did something similar... I never did write down the code, though. Maybe ask for permission to save a log on the windows environment?
I'm a little busy at the moment, as I'm participating in the Google Code-in, but I'll see when I can get around to doing it...