Stephan, Since you're one of the directors of the Python Software Foundation, could you let them know about this discussion in order to get their approval? If they agree, maybe you can tell us where and how to held the contest.
Just one thought: I think that it would be good to not determine a deadline for the contest. We should let anyone submit their designs until a clear winner shows up, or until Guido or the board of directors chooses a winner. -- http://mail.python.org/mailman/listinfo/python-list
