I've seen many coverage maps that were done by consulting engineers. They were accurate based on M-3. I've seen some based on proof of performance data. I've seen ones done by sales departments, and those are pretty obvious-circles, ellipses, etc. The one R. Fry linked is a QSL card signed by Ed Buterbaugh. So I'm surprised if it isn't accurate or mislabeled.
The five tower configuration of CKLW looks like something Carl Smith would have come up with. It's a parallelogram with a fifth tower in the middle.
Within 250 miles or so, the skywave pattern is much different than the groundwave pattern. What you get in Western Michigan is high angle radiation. The lobe to the near north shifts substantially counterclockwise in the night pattern also.