The biggest issue Hillary has is that other women hate her. Especially red state women. For any reason you can imagine, none them what I would call valid.
Oh, this subject is complex and fraught with peril. I think the main thing, obviously, is feminism that has done some work, but not completed it. It is interesting that so much of the world has had women leading democracies and the United States I think still has some time to go unless Kamala inherits it. And maybe that would be the thing to break the ceiling?
Just looking across my lifetime, you can see a lot of different solutions to the equation of how a man becomes electable as President. Nixon has been so strong as President, but corrupt. Jimmy Carter was smart and honest, Reagan was steady and charismatic and so popular that HW got to be a sequel. Clinton was smart, but also cool. W seemed like you could have a beer with him. Obama was inspiring and focused. Trump was a 1%er who had the little guy's back. Biden was a career statesman.
There are not so many solutions for women and I am not sure how to profile the woman who will both win her party's primary and then win the general election. It is easy to suppose that all else being equal, being a woman would be a secret weapon in the states that are hard to turn. But men and women have strongly supported men who they didn't like for all of the reasons in the previous paragraph and I don't think they'll vote for a woman they don't like. Sexism is certainly sitting at the table, but when I went on vacation to Washington, DC about 20 years ago, I was in the hallway of a Senate office building to get tickets to tour the Capitol. Hillary Clinton walked down the hall all by herself and passed within a few feet of me and never gave any outward sign that she knew I was there. She wasn't on the phone, she wasn't talking to anyone, she wasn't moving quickly. I was with a few people and she just didn't care that other human beings were there. Just a few minutes later on the way out, we met Ted Kennedy coming the other way. He was walking with half a dozen people I didn't recognize. Aides, I guess. He smiled and nodded to us. Maybe he was just a more savvy politician. That wouldn't be nothing. But I actually think that for whatever anyone thinks of the guy's politics, he genuinely liked people. And Hillary doesn't. She isn't even good at pretending. I think people (men AND women) can overlook that in a man and are not ready to overlook it in a woman.
By start contrast, Sarah Palin seems like a lot of fun. She is energetic and chatty and not uptight at all. She didn't seem smart at all. No foreign policy experience, but she'd been governor of a State. She was George W Bush. But it didn't work, because America wasn't buying it.
Kamala Harris reminds me of Hillary. She succeeded in becoming Vice President, so she's the most successful so far. But I really am not sure why she got the nomination and I am doubtful that she contributed to the win. She was an early dropout in the primary because she just didn't have a following. Maybe Biden had worked with her and genuinely thought she was the best qualified. I uncynically say that I think Biden wanted a woman running mate and not simply to draw votes but because he really felt that a woman deserved a shot at it. He put a lot of women into leadership positions in his administration and sent one to the Supreme Court, AFTER he'd won the election. I haven't been a very good spectator, but right now all I can remember is that Biden put Kamala on the border early on and she didn't impress. She hasn't made a headline positive or negative. But listen. She's the dang Vice President of the United States, a former state Attorney General and Senator. Her resume lacks nothing. People who know only one part of her job description know she is supposed to replace Joe if he needs to be replaced. But Joe had a bad debate and people thing he needs to be replaced and I haven't been hearing people in power saying Kamala should get the nomination and I think it is a fair bet that they would if she were a man. Isn't the VP the really obvious choice?