Love the concept of this game. It reminds me a bit of a game I played avidly for some time called the Ungame. Well done.
I saw these things listed below in the text which prompted the questions listed.
The Wheel Of Fortune...Before you start, confer and settle on one of it's four modes.
Should this be its, rather than it's, which is a contraction of it is?
COINS: Try to proof useful.
Should this be prove, rather than proof?
I also noticed that the Emperor and the Empress have the same question, "What are you ashamed of?" Is this intentional?