Additions to the task were also made by Dane Ehlert as well @daneehlert
Here are the questions I asked the students about this situation with the expectation to prove each response...
3) Is Squirrel Man Faster than Usain Bolt?
I did give them an approximation of the length of the race since we have not explored the Pythagorean Theorem...
Through the conversations with my students, I found out that the trickiest parts was to simulate the head start. Many students were confused how to tack that onto and/or subtract it off from and who the addition or subtraction would go to. That is always the interesting part of doing these tasks...you can scour over the task for hours trying to anticipate pitfalls (which is a good idea by the way), but you will never catch them all.
Here are some work examples from my students for your viewing pleasure. I attempted to find different routes for each question so you can see the variability. I will also leave you with one of the greatest quote in the history of quotes (from the second video on this link) that middle school students really enjoy (if you work with middle school students...you can imagine the response).
"And here comes the squirrel...he smells nuts!"