I forget who won mine but it was really fun! I think this would make for some very interesting fanfiction! It'd be even cooler though if the simulator took into account things like their abilities or personality traits which could enhance or decrease the chances for certain events to occur. For example, Klonoa being more likely to drown because he can't swim in water, Pango being immune to backstabs and less likely to die from land mines and Guntz's speed making him more likely to sniff out things or outrun things like Tracker Jackers, but more likely to die against a group due to being a loner.
Another minor criticism I had was that the simulator doesn't seem to take into account the inventory of the characters. Guntz died in one of my playthroughs despite being armed with a sickle, medical supplies AND an explosive against an unarmed opponent.
Still love the idea of this, though. It was fun to play, I just wish it could be customized a bit more to tell a bit more of a story or just be more cohesive. Maybe you could effect one player per day? And depending on your decisions you get multiple endings? (ex: more than one person surviving. the rebellion arc of the second part of Hunger Games?)