Thanks for that scholarly and thoughtful comment. The intro to The Roads Must Roll is an example of that complexity. It starts with a labor union meeting arguing for the workers to strike, and then a counter argument that could be an unacknowledged contribution from Ayn Rand. And this was from the presumably progressive early Heinlein.
I'd like to be there for a debate between 1940 Heinlein and 1980 Heinlein. I wouldn't be surprised if that event is scheduled for the Howard family reunion at the end of time and Time Enough for Love.
Which, to be fair, is also a Socialist utopia couched into a lot of Libertarian jargon/perspectives (to well beloved to mock extremes such as the way that society handles, say, the "Extreme Libertarian" approach to the incest taboo).