I find Jake English to be a strange anomaly in the story. How is it that he is able to ascend with, what can be assumed to be, his regular body considering that his dreamself was killed before entry? Also why is it that he's so closely linked to the cherubs, in terms of their similar vernacular, being destined to beat Caliborn, and the fact that full grown cherub wings look very close to the hope aspect symbol?

Jake ascended on the Quest Crypt, it’s the only place you can ascend with no spare lives it seems, but he’s still an anomaly in that he shows us it doesn’t need to be your Dreamself dying on the Crypt, a normal body works just fine too.

It’s not just Jake though, Dirk is closely tied to the Cherubs as well, and to a certain extent, also Karkat! And it’s all because of the Cherubs’ ties to Abraxas and Yaldabaoth. Hope and Light are both concepts tied to Abraxas, to the World of Ideas, so with English being the Yaldabaoth of Homestuck, it’d only make sense the Hope Players had a prophecy about taking him down, one which is technically fulfilled during the Masterpiece! The wings may be stylistic, they are just wings after all, but they could hold some meaning.

Dirk, and more specifically AR, is tied to the concept of the Yaldabaoth as well, and would you look at that, eventually AR becomes part of Lord English himself. Karkat is implied to have had Abraxas as his Denizen, and he’s tied to Cherubs as well- His grey text is the exact middle point between UU and uu’s, his blood is Candy Red, but a mutation of Lime, providing the green-red duality… There’s. So much to talk about with these three, their ties to Gnosticism, and the Cherubs’ ties to these concepts. @revolutionaryduelist has done some amazing essays on the topic.