The point about insurance is not accurate. In some low-lying areas, these statements are accurate, but even in coastal areas it is far more common to have a finished 1st floor with the standard insurance rules. It all depends on the flood/evacuation zones.
His management is thoughtful! Plotters are cheap, but the entire chain of events leading to an effective sign being installed is almost certainly higher than this one guy spending a few hours on a sign.
Design Thinking is just solving problems (and creating new solutions) from the end-user's perspective. Some people are naturally good at it, but others need some structure to make it happen.
Waldorf is all about fostering imagination, so they try to limit anything that comes with a pre-defined set of ideas that tell you how to interact with it. A plastic firetruck already has an identity; an unfinished wood truck can be anything.
Swear jar is a great analogy. Also, that'll be $2.
It's a game mechanic that encourages people to be more thoughtful about how they think about a problem. Not perfect, like the swear jar, but it has some value in changing behavior.