This discussion may contain spoilers!
Now, I am not obssessed about Homestarrunner.com's 'canon', but I know people who are, and I am asking this question on behalf of them.
Can we consider the events in the game to actually have happened in the canon of Homestarrunner.com? That there is a Race To the End of the Race Race? That Homestar Runner really ran naked? Well, most cartoons can. The problem is, Strong Bad himself sold the license to make this game, and he has not confirmed if the events happened in Free Country, USA.
Not that he actually would. Strong Bad's belief in 'realism' usually involves him having muscles and him dating hot chicks that flies to Mars. So, no, the game won't be realistic by his standards. But is Telltale basing this off 'real life'? Or is Telltale making stuff up in order to sell games, in the same way that Strong Bad usually lies about his life? Is the game canon, when you consider its origins?
Remember, I myself don't care, as I believe this is a cartoon and people shouldn't overthink. But someone WILL overthink, so let get this question over with NOW.