My wife's a Norwegian Lutheran and I always enjoyed listening to the tales from Lake Wobegon, but in quiet moments of reflective listening, I have always thought that there was more than a little bit of condescension and smugness in Keillor's schtick: that his mocking was not that of a knowing insider joking with others sharing the same background and values, but of an outsider making fun of rural people and values for an audience of urban professionals who would no more identify with the values of Lake Wobegon than they would with the Ku Klux Klan.
BINGO! You nailed it right on the head.
From the first moment I heard Keillor, I knew that there was something that bothered me about his humor. It took me only a little time to realize that he was having inviting his audience to have fun by laughing at this characters, not with fondness, but with malice. If you listen carefully, it will be immediately obvious that Keillor is not laughing WITH the people of Lake Wobegon, but AT them. His monologues are an unending, ironic put-down of fly-over country people and values. Why, the inhabitants of Lake Wobegon even think that all the children are above average, obviously something only a poor, uneducated, rural hick could believe. Even the name: Wobegon, is an indictment. Only lifes losers would stay in a place of woe.
What fools people about his monologues is the tone of voice in which they are delivered: a slow, measured Midwestern drawl that lulls. It is the same technique that Dashle uses in his attacks against Republicans. The tone is low, measured and muted. But the words are designed to draw blood.
I've never been able to accurately articulate just why I ceased enjoying his humor -- which, at first, had seemed so fresh and insightful.
Your #31, however, is right on the button. I come from a small town in Oklahoma and Keillor's storytelling revealed some humorous insights I could relate to. Eventually, I realized that he wasn't laughing with us, but at us, instead. He was mocking the very people whom he purported to admire -- biting the very hand that fed him.
Garrison Keillor is an ungrateful wretch, a very nasty man.