Why not?

IIRC, in Canada, its illegal to ask those questions during the application.

Then, when HR is doing their diversity calculations, he boosts their employed woman trans numbers.

Don't see him loosing out much.

"A crossdresser can dress like a woman in the weekends, and dress like a man during the week. Who is the goverment to tell me to keep the same sex all the time?!!!1"

how about legally recognized "contextual gender", i.e. a woman while driving the car, a man while applying jobs etc...

/s

A male pretending to be a female has an edge over males,females and females pretending to be male when applying for jobs.. Atleast in an unscientific study by interviewing.io

Depends on where the application goes to. Many companies want to appear politically progressive.