Josh is too stupid and solipsistic to ever roleplay as a woman or anyone else really, he's obsessed with his own ideas and how reality effects HIM and can't imagine what other peoples' interiority or concerns might be like. Honestly the kind of creativity where you can mentally and emotionally skinwalk as a person with a dramatically different lived experience than you is really rare generally, the only people super good at it usually become fiction authors. Take the average person who can't do that very well and push it even further to the left on the bell curve and you've got Joshua Moon.
Funny possibility if you run with the frankly insane theory he's socking as a mentally ill radfem is that childhood abuse gave him dissociative personality disorder.