Just a crappy roof install.
That metal flashing just caulked on top counter flashing is, indeed, called “Chicago style”. That’s pretty much the only way they do it around here. When I tell the roofers, they just look at me like I am from Mars.
I know a couple of brothers who are 3rd generation roofers around here and have, in the past, done outstanding work. Recently, I inspected a couple of roofs that they did and found their workmanship lowering itself to the crap we normally see.
I called them and asked them what was up. They told me, “Yeah, we know it was not a good job, but it is what everyone else is doing.” I asked them why they have lowered their standards. They told me, “Look, you can be the bes quality roofer in town, but if you don’t get any customers you just go out of business.”
In other words, there are so many sub-standard roofers that low ball everyone else and wind up setting the standards lower for everyone else, that the general public come to expect lower prices and don’t hire the good, professional roofers anymore.