@lyndis; i'm seconding nautilus here: you should definitely reread the epilogues. jade and jane aren't perfect or flawless within them, but i do think they deserve a bit more grace. especially jade.
i certainly have to second margot on her thoughts on jade and davepeta, though i think with roxy its more complic8d. to be very upfront here i'm a transmasculine person; so take that as you will. though i wasn't around prior to the epilogues i know many people read roxy as textually transfeminine. originally i believe it was due to the "XY" being teased in her name reveal, as shaky and unwieldy as that would be to introduce a trans woman. take that with a grain of salt, though... since this is essentially a secondary source. i believe there's also a lot to be said with regards to "surrogate motherhood" with roxy, though that can definitely go either way re: transition.
i do wish that meat roxy's transition was handled differently, though. he's so boring designwise :/ and maybe it's just the amount of screentime he gets, but i feel like he loses a lot of his individuality. i've seen people call him "dave lite" and quite honestly i'm a little inclined to agree. transition doesn't entirely change a person, but i would've loved to see more change with roxy, or just more of him that wasn't gender or being around davekat. i want to see him gush about wizards or try to get in touch with dirk or talk about classpects with callie. meat roxy is a nothingburger.
i've seen a lot of discussion on tumblr of homestuck (proper) being textually transfeminine, which i think is HIGHLY compelling-- whether just by virtue of hussie herself being transfem or the very fact that the oppressive & antagonising force in the story values masculinity and either forces it upon characters or discards characters who reject it. there's very few characters that i personally see a sensible transmasculine interpret8ion of, and even then.. most of them i could also see as transfem. karkat, for example, goes to ridiculous lengths to hide something that society would shun him for and tries his hardest to be the boot rather than the ant underneath it, which i read as mimicking the experience of stealth trans men, especially those who take on misogynistic behaviours in order to pass. at the same time, though, she can also be read as a trans woman who's VERY deep in the closet and tries super hard to conform to her assigned gender!
it's just... when something is subtextual, like the transness in homestuck proper, it's more interpretive and just there for those who want to see it. it can't be criticised because the intentionality is NOT confirmed. but when something is made explicit, like jade or roxy, the intention is there and everyone who interacts with the story has to face it and is given that character, for better or worse, as a representative of that specific experience. i can't speak much on jade more than anyone else here, as it's been plenty of transfems voicing their thoughts (Thank Fucking God This Forum Isn't Insufferably Transmasc), but i think roxy could've been done better.
-- real slim shady