The thing about Heinlein, is he definitely went through this crochety phase where he was just sure that engineers and the military would end up running societies (esp. Starship Troopers and The Moon is a Harsh Mistress, though I generally like the latter one). But then he went all 70s with the pansexual books he wrote after that (I Will Fear No Evil, Time Enough for Love, Number of the Beast, To Sail Beyond the Sunset). Friday is probably the least creepy of these late books, but it is still a bit odd to see a male author "Mary-Janeing."
I'm sure I would be a lot less impressed with Heinlein's wisdom today than I was as a teenager.
Personally, I thought Starship Troopers was just as good as The Moon is a Harsh Mistress. I didn't mind that part of his career at all (although Stranger was just too much); it was the later phase (won't bother naming the offenders as you already have). Though I Will Fear No Evil certainly deserves special mention as particularly pathetic. I know Number of the Beast is often held up as his worst, but I'd much rather read that the the embarrassingly bad Fear No Evil. But even then, I thought Friday and Job: a Comedy of Justice were worth reading.
In the long run, I'm afraid Heinlein will be remembered for his hand in creating the conventions of the genre rather than for his actual writing. Except for All You Zombies; criticize that one and I'll turn back into a teenaged fanboy and go batshit!