Good idea. Check out the video here: http://blog.quixey.com/2011/10/03/quixey-challenge/

Which is staged. I wonder whether the real challenges are in similar style and difficulty. Looking at the problem in the video it would help to just quickly pull out template code and compare it. Would help to have an easier way to know whether this is something I could accomplish or is completely over my head.

$100 bucks, I could need those.

similar in scope and, depending on your grasp of the algorithm and python, roughly the same difficulty +/- a little bit.