When I was a kid I heard about someone who liked for people to beat him with a rubber hose because it felt so dang good when they quit. I’ll bet this activity has similar dynamics—feels so good when it’s over, makes you appreciate your snuggly bed more.
And it is, no doubt a conscious choice (regarding the drawing style not being realistic), given that Watterson has amply demonstrated the ability to draw realistically.
Honestly, I made part of my living as a copy editor, and I didn’t notice it. I think the nature of the handwritten script helps it slip past as well. a) I understand how something like that happens, and b) do the syndicates not have editors any more, just as has generally happened with newspapers?
Sounds similar to a town in Maine Garrison Keillor talks about, Piscacadawadaquoddymoggin.