First of all, fuck Monopoly. My family had to toss ours because the bickering got so bad. But that is a tale for another time.
Anyway, I really like the format. Wikidot code is a mystery to me, but this looks really good. The biggest thing I would do to improve upon it would be to include some kind of testing log as an attachment to one of the emails. I feel like that would show the kind of benign nature of the most insidious board game known to mankind (I'd play Jumanji before ever playing Monopoly again). Other than that, it's a cute tale, funny once you get it, and I feel this has potential
Good luck! Now if you'll excuse me, I'm going to laugh at the mental image of a prison economy running off of Monopoly money.