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I think you don't fully understand the intention behind the argument. Rather than being part of some mathematical deeply logical proof, it is much more an appeal to someone's common sense or feelings.

Generally, the conservatives like to portray themselves on trans issues as the common sense side. Think of when they extend LGBTQ with all sorts of weird letters, rolling their eyes. Or think of Dave Chappelle's punching down specials. Or think of The One Joke. And this is a very successful starting point, because most people are not knowingly interacting with trans people, so to them trans issues are already a bit unfamiliar, or weird.

The idea behind the argument is to have the answerer realize that in fact their position is not the obvious one, and that their position is actually weird. And this is highly subjective. The point is not the answer, the point is the hoops they'll have to jump through to get to a satisfactory trans-exlusionary answer.

It's subjective of course, but it's very hard for someone to write a 20 page definition of gender and then follow that up with "duh". Or to write something like "producer of the large gametes" or whatever and feel like a normal person.

Car is one of those repurposed words. It used to mean any wheeled vehicle until around 170 years or so ago. Automobile was used at first for cars. When I was young automobile or auto was the preferred term. Car or auto can be used for motorcycles or trains, there are just better words for those.

Human sexuality is a spectrum and not an either/or situation, and should be treated as such. That being said, a chromosome test would answer the question in over 95% of cases, I believe. I could be wrong about this, so anyone with a better understanding, please correct me.

No hate, but I love a good debate if you're up for it.

Scenario 1:

Great points, honestly. However, even in this scenario where someone manages to cover all of the bases and managed to create an exact list of what it means to be a woman, it would be impossible to disqualify trans women.

Scenario 2:

I'll get deeper into this one since it's more realistic.

I bet you can't define a car

Vehicles are defined by their frames, and the regulations that revolve around those. I can tell you with absolute certainty whether a vehicle is a car or a truck based off the frame. But this isn't the point.

Does that mean we all just get to [define words ourselves]

Actually yes. Words gain their definition by how they are most commonly used. You learn a word based off its definition, but the word gains its definition from use. This is how Shakespeare managed to invent so many words in English. He just started using them, and when people asked what they meant he told them and they started using them. This is also why "literally" is defined as "not literally" by Webster dictionary, or at least it was around 2016 (may have changed).

As a matter of fact, entire languages have been built around this concept of redefining words. Most of German is just portmanteaus that were understandable enough to be considered a word.

In this particular case, the words "man" and "woman" is slowly being redefined by society to be more inclusive of trans people. Fighting against the progress of language, in this scenario, is nearly identical to fighting against the progress of trans people.