In some cases, it’s a broad umbrella term that includes a wide variety of folks who’s genders are questioned (thus my definition above), such as crossdressers, butch women, transsexuals, etc. While most folks define it as such, you might find more usage which focuses specifically on those who identify and present as a gender other than what they were assigned at birth, often but not always with the aid of hormones, legal documentation change, etc.

So we have a category of people who are often included in definitions of transgender and often excluded from discusions of transgender folks. It’s awkward, I don’t advocate it.

This new take on defining the term is an experiment to try to draw a new line. If there’s anyone out there who might doubt someone’s gender, then they could see themselves as trans. “Jo” certainly fits that, as you say that she frequently passes for male, there are lots of people who see her as not a woman. “Bob” might only be at risk if people discover he’s crossdressing, but I’ve definitely seen folks who would say he’s “not a real man” because of it — not to mention folks who assume he’s on the first step toward transitioning. But just because someone can call themselves transgender doesn’t mean they have to. That’s where self-definiion comes in. And if there’s literally only one person in the world who invalidates a person’s gender, they might decide that the term transgender communicates more misinformation that information about themselves.

As for Bob being a “transgender man” and Jo a “transgender woman”, I disagree, but only but only becuase those terms have taken on more of a meaning than the words mean individaully. Bob may be “transgender” and may be a “man”, but if he calls himself a “transgender man” then most folks are going to assume that he was assigned female at birth, which your example implies is not the case. So while he could fit the definition and press the issue if he wanted, our current usage of terminology is not as flexible. (Note that the information in the definitions about “trans men” and “cis woman” are given as examples, not as definitions, so they shouldn’t be taken as applicable in all cases).

In any such case, reality perpetually defies definition and strives to move beyond any constraints we try to place on it using logic. I think no matter what definitions are used, there will always be folks who fall outside of it — again why I rely on self-definition.

I provided two examples in my discussion — “Bob”, a heterosexual male-to-female cross-dresser who is very clear in his mind that he is a man. “Jo”, a stone butch woman who frequently passes for male, without even trying. She is very clear that she is a woman.

In that discussion with both seem to agree that “Bob” and “Jo” are both transgender individuals. And given the self-identification that I’ve presented, we’d have to agree that “Bob” is a transgender man, and “Jo” is a “transgender woman”. If you disagree, please explain.

See the problem here? Bob says he is a man, who is going to disagree with him or invalidate his gender? Jo says she is a woman. People might complain that she is “mannish”, but who is going to say she isn’t actually a woman?