On the question of who would have been the better president, Hillary just had a much better track record at actually governing imho. But ultimately she was unpopular and had a scandal brewing that would only cement her unpopularity. And like, end of day, winning against Trump was most important.
I find any populist politician electorally very frustrating because anti-establishment messages resonate with voters very well but that’s because it can produce a rainbow coalition of people who want to tear it all down but no consensus as how to replace it with something better.
I honestly don't think he would have won. Sure, he is a guy and that mattered probably the most, but he's also someone who couldn't even get democrats to vote for him, so...