It is possible to get past 5-2 without dying, but I'm not sure how I did it. It might be depended on which animal you're using, but I'm sure it's partly determined by 'see-saw'ing and garnering enough momentum for it to keep going. Can't imagine getting past 5-1 without dying though.
I scored it according to how the game was made, and I think it was made rather well and did exactly what it was intended to do. 5/5
My only gripe is that Realist ought to be renamed Swindler. He was 2k under me in endgame, and yet on his last roll, earns over 3k and steals the win.
http://img99.imageshack.us/img99/290/cheatingrealist2ba8.jpg
On the other hand, Cautious is far easier than Reckless.