Greenland is a beautiful nightmare

It's funny to me that in portraying Indiana as a "blank state" he's highlighting one of the most beautiful parts of the state (the route through the Dunes along the Michigan lakefront; if you've seen "Road To Perdition", you know what that area looks like). It's not important to the article, a complete tangent, but I can't not call that out.

Then again, that stretch also has Gary.

Having grown up in that area of the Midwest, I largely agree with the author's categorization, except that "people on their way to somewhere better who got tired and decided this was good enough" describes a LOT of the midwest, not just Indiana. Significant chunks of Michigan, Ohio, and Missouri, most of Iowa/Kansas/Nebraska, etc.

If you read the history of westward expansion, "got tired and decided this was good enough" is literally true for how much of the area got initially settled (by white people)

Yep. Even worse, the problem is recursive: a town I lived in for a while growing up, Vandalia, Ohio (a suburb of Dayton, itself not exactly a booming metropolis in this millennium, but I digress) was settled by westward migrants aiming for Vandalia, Illinois - a town in the absolute middle of nowhere that just so happened to be the end of the National Road, presumably because the road builders got bored and/or ran out of money. Anyway, the travelers got bored and/or ran out of money on their way to Illinois, gave up, said "good enough", and named their new Ohio settlement after the place they failed to reach.

The Midwest is many things, but for quite a lot of it, "where anyone really wanted to get stuck" is not one of them.