I think you may enjoy this classic text on the topic, it explores these questions in quite some detail: https://janiceraymond.com/the-transsexual-empire

(That page has a link to download the PDF if you're interested, but also here's a taster in the form of a book review at the time it was published: https://www.nytimes.com/1979/06/10/archives/male-and-female-....)