You want character discussion how about we theorize about what character Winter thinks could be trans.
My vote goes for Maud.
The big kink in the plot armor of that theory is how Maud would have had to have been exposed to a sufficiently powerful source of chaos magic. A source powerful enough to allow her to magically have a working-womb -she does in fact have a child in the game's canon. Her tragic back-story as a poor woman with non-obvious magical abilities or connections seems to invalidate the thought- irregardless of her tomboy attitude.
If we are really going to go down the path of theorizing about this though.....how about Shaya?
~She seemed to have a pretty firm grasp of how to use a dick when she gave it to Jez with a strap-on.
~She is also the only character who canonically went through a transformation powerful enough to have made that transition.
~She seems simultaneously to have been willing to do anything for Jezaera but also seems to regret her decision on some levels.
~She is very good at obscuring the truth and could have lied to Rowan about any part of her back-story.
~She is jacked
Do I actually think Shaya is trans.....no ; but it'd be the plot-line where it made the most sense.