He would have easily won. But it isn't because his vision. It all has to do with likability.
Clinton had none and that is how she lost to a complete nut job. If someone likable had run then they would have easily beaten Trump.
They are a private organization so they can do what they want. But if the kid had been there a month and the other kids were fine with it then I don't see the big deal it letting the kid stay. As long as they are open about it and still accepted then whatever. If they were dishonest about it then it'd be a different issue. That said I don't see any reason they have to admit people who are biologically female either. They are an exclusive group after all.
The logic used by the cops basically justifies shooting any cop that comes into your house since you could easily feel threatened they might harm you. Idiot cops and idiot judge. But then what else is new. Sucks there are so many bad cops that make it all the worse for the ones that are actually good guys doing their best to protect people.