Since I interpret the creativity category as originality -- this goes as a 5 for that -- never played a game like this before.
Uh but anyway, some useful additions to making this more playable -- I can't even see the full window titles because they're cut off and I can't make the windows bigger because it doesn't let me resize them. After you get an achievement, it would be nice to know what exactly I did -- for example, I'm not actually sure what 2 Lucky Rolls even means. It would also be nice if you could see all your hints together in one place, especially because it doesn't seem like they appear again. Also, and most important, there should be a close all windows button.
So I really like different and subversive games, and this is really cool, but there are definitely some improvements that could make it really fun and interesting too.