Note: I am starting this blog as a working outline for an upcoming panel discussion on the above title.
A little background I grew up in family of strong, independent, intelligent women going back at least three generations. My great Grandmother supported a large family as a writer, composer, and nursery school operator at the end of the 19th century.
The first Heinlein I remember reading was an ugly duckling rework in F&SF that turned into the The Star Beast (1954) which I bought as soon as it came out in paperback in the mid 50's. I resonated with the idea that the main (human) protagonist in the story was a young woman who overcame the prevailing attitude that women were basically ignored as adjuncts to the men in the story. Teen Betty Sorenson was introduced to the story to take charge of a bunch of men, adults and her boyfriend, who were botching an accidental disaster caused by the large bored extraterrestrial Star Beast. The rest of the story is about Betty making fools of the cartoon men in the story to save the world by making friends with the Queen of the powerful extraterrestrials. Much of the story was playing with the conventional role models of males and how 2 strong, competent females can use feminine social and nurturing solutions to solve problems.
In many of his early works the obligatory male protagonists seem to be continually bailed out of trouble by females who are strong, competent, and continually violating the traditional female role model of subservient companion. "Jack" in "Tunnel in the Sky" Maggie in If this goes on... Eldreth in Starman Jones.