Jonathan, I'm going to agree with most of your statements. But I'd like to tell you a little something, because you might find it enlightening.
You said, "Everything that makes Python great doesn't mean much to managers -- will they care about significant whitespace?"
Recently, I did a risk analysis for Lockheed Martin where we compared some of the major up-and-coming popular "scripting" languages. I chose Python, Ruby, Lua, Ocaml, and Erlang as examples of languages with strong but somewhat hidden support. These are the folks that I feel are the up-and-comers. So we did an analysis, comparing stylistic differences, typing, testability, readability, usability (as in number of libraries), and maintainability (what companies could offer sustainment with these languages). The risk scale went from white (0 risk) to green (not too risky) to yellow (risky) to red (too risky).
Python was the only contender in this list that's in the green. When I spoke with middle-line managers and the hollow once-engineers who hadn't done any real work for years--now doing "engineering management" and "proposals"--Python had the most favorable impression. They loved the idea of things like significant whitespace, because (and I quote this), "It makes people's code more similar." It also helps reduce the burden of people who draft up code standards. Other popular features were garbage collection, familiar syntax, and the fewest "new methodologies" for programmers to learn. Now, maybe my bias is showing here, I'm not a huge Python fan. For that reason, I had the other engineer on my project, who is a big Python fan, handle Python. I thought it was interesting that the same things I thought were weaknesses of Python turned out to be strengths in the eyes of our review.
But as I was doing this comparison, I realized something. If the Revolution were to happen today and Java and C++ were shot in front of the wall, Python would be one to rise to dominance. Because, when you get right down to it, Python is the least different.