I think that the most real (which also makes it heartbreaking) unambiguous clearest solid evidence would be from Str's DA days, even tho it's very old at this point.

In this post js-addiction goes through Str's DA account, and among all the evidence of him being gay/bi there are some things that are very clear transfem... I show them here, but you should go through the whole og post linked, just amazing stuff in there...

cute little girl edit... called pretty... teen boy or masculine female :3

GOOD GIRL BRACELET. "Are you a boy or a girl?" "The world may never know :'<" ...................................................................

there is also this, Str having 'female' on his profile... typical gender DA stuff but hmm also, cheerleader :) <3

So, in addition to Steebs very open gayness it seems there was actually a lot of interesting stuff happening regarding gender in his younger years.. Looks like he enjoyed being perceived as a girl on the internet(!)... wore a pink "good girl" bracelet... tried on dresses... all of that makes me sooo so :3333333 🥰🥰💞 I think this is getting REALLY close to being transfem without fully/openly commiting... so all of that is absolutely insane

Besides that, the current day it gets much more vague of course. there are only echoes I would say, things that don't necessarily have to mean anything and be giveaways, but they do have that something in them that can make you think... like what you mentioned, him choosing to play female characters a lot :) or making himself in tony hawk game and giving himself a fucking girl symbol sdfgh

Sometimes he says something that will perk our ears up, I do remember us here having quite a few collective "estrogen would have saved her" moments w/ Str... I wanted to provide some, but I cannot find one when I need it of course. if i happen upon some I might add them here