Your two points are the same thing. In the old vernacular, a woman is someone who was born with the outward appearance of a biological female.
Biological sexes aren't transphobic to acknowledge, it's just transphobic to insist biological sex match expressed gender. Gender is purely the socially constructed identity side of things, so saying the feminine gender is the same thing as saying the societal constructed norms often seem as female.
It is interesting to point out if you look up definitions from very old dictionaries for example from the first few editions of Webster gender and sex basically mean the same thing it wasn't until recent years that they got separated in definition. (And by recent years I mean in the last few decades)
My point is it's not difficult to define what a woman or a man is. It's just that Matt Walsh doesn't know what a woman or man is which is beside the point because he's an idiot.
i think fundamentally, if we're arguing what the definition of a woman is, we need to consider social gender constructs, because female is to do with sex. Womanhood is more about maturing and coming of age. I.E. what is socially expected.
Basically, it's dependent on current sociological theory and definitions, as well as the commonly accepted terminology. So to quote matt walsh "nobody fucking knows"