Number 3 has absolutely no place in an otherwise solid post. Cuckold ffs.
I realize that is now a charged term and I probably should have left it out but I am analyzing this as I would as a political strategist. And it is a valid strategic concern. Have you seen the documentary
Get Me Roger Stone?
The disinformation operators have absolutely zero qualms about using anything and everything from the most distasteful outright lies. If I was advising the DNC last election, I truly believe it would have been a mistake to ignore the counter-attack that Trump effectively used against Hilary whenever the misogyny got brought up.
I am not saying that I like it or personally agree, but as a strategist if I look at Hilary using that misogyny angle against Trump, the counter is very obviously going to be something along the lines how her husband did many of the same things and she stood by him and defended him. Or going even further as the Bannon-Stone crowd loves to do. Its just not a strong strategy for Hilary Clinton to use against a political opponent whereas another cleaner candidate could wield it more effectively.
That counter is going to resonate with a lot of people because Hilary was so unpopular for so long among close to 50% of the population. If Obama was making that criticism of Trump then Trump has no clear retort that can gain traction, even among his base. I really think it would have been poor strategy for none of her advisers to bring this up and adequately prepare for it.
This is actually why I didn't get into politics as work because analyzing distasteful issues like that is kind of important.
EDIT:
I realized that I should also clarify the personal baggage and policies really overlap as well. She has too many issues where she supported one thing then tries to go the other way so the counter is always going to be "but why did you support this back then". And these aren't issues where its easier to flip and just new data changed my mind. They are more long lasting issues that reversing opinion on just begs the question of trust.
A candidate with a pattern of defending her husband from misogyny but now attacking another for it, supporting mass incarcerations and private prisons when it was politically expedient but now reversing that stance when its not, supporting Wall Street and corporate welfare going back to the 1980s when she was on Wall Mart's Board but now wants to reign in big banks because liberals do, bought into the propaganda for Iraq War when the mood it but now ensures that wouldn't happen again, etc just loses trust on many angles. Sadly, while distasteful the personal angle is/was one of them and a powerful one in some cases if the candidate is unprepared as in this case.