I think I understand what you're saying about the pricing. Am I correct in saying, then, that if the odds are 90% in favor of my living through the contract, the "No, smeej won't die today" price should be close to $0.10 (again, ignoring fees and the time value of money)?
If the hitman tries to buy in with 10% of the total funds already in the market, the odds/price are going to shift hard. It's going to devour a huge chunk of the order book. Any market that suddenly has someone come in at 10% of the whole market value is going to get a massive trading wick. So yeah, he'd get some shares at $0.10, but he's probably going to eat the open order book to a much higher cost. He can 10x some very small portion of his money (however many shares are on the book at $0.10), but he can only 5x his money at $0.20, or 3x at $0.33.
Even if we assume he does have $50k to dump into the market, I still don't see how he's going to more than triple his money, which is a heck of a lot less than taking the entire market's value as though it were a bounty.