I always considered your comment about Purdue never making a Final Four as totally ridiculous. Sean Connery once declared that he would never make another James Bond movie but he did. It was called "Never Say Never Again." Events that seem unlikely to us can and do occur fairly regularly.
However, you have topped yourself with the post that "Milan is arguably the most famous high school in the nation." That one is almost beyond absurd. I have lived in many parts of the USA. There are some well known high schools. Examples would be Boston Latin, Bronx HS of Science, Stuyvesant and Horace Mann in New York, Sidwell Friends, St. Albans, DeMatha and Georgetown Prep in Washington, DC, New Trier, Chicago Latin and Francis Parker in metro Chicago and Harvard-Westlake and Mater Dei in LA. But there is no way Milan is found in that company. In the movie, that is not even the name of the school. People in Indiana maybe aware, but outside of the state an extraordinarily small number do. Your post is a howler.
While "Hoosiers" is a good movie, it is not the best in its genre. "Chariots of Fire" was nominated for 7 Academy Awards and won 4 - including Best Picture. "The Natural" was nominated for 4 Oscars. "Field of Dreams" was nominated for 3; "Hoosiers" for only 2.
I get that you really like the film but you grossly overstate its place among the general public.
I would strongly advise that you not make those bets and save yourself a bunch of money.