I caveat that I have not read *all* of RAH's stuff, really just the best-known stuff. He's commonly thought of as a libertarian, but I always got the vibe that he sympathizes with the working proletariat -- if not organized labor -- against the elite. He bought Philip K. Dick a typewriter and loaned him money to pay off the IRS. (PKD was broke a lot of the time, as one might expect.)

Money shot in this article: "Isaac Asimov, who knew Heinlein from the mid-'30s on, was convinced that his personal political views were largely a function of the woman he was married to at the time."