What a about Caliborn makes him so cool in your opinion?
Go keep track of his progression as an artist alongside his development as a character and think about how these are intrinsically linked. Ponder the fact that he is both at his most obnoxious and at his most amateur when trying to ignore his unique style explicitly brought on by his canonical learning disability and mimic others rather than truly be himself. Consider how his explorations of art are genuinely cool, not a bad thing, and how we get some really neat multimedia stuff out of it.
Caliborn may be a shitty little teenage wretch but the way he is portrayed as an artist and as a disabled person is both really good and very real. It comes from a place of love. His learning disability is handled with a degree of gentle care that you would not really expect from Hussie. The place Caliborn's art style ends up in is so fucking sick and I actually unironically love it. The technique he uses is really interesting. It's intentionally reminiscent of an Etch-a-Sketch, and I'm a little obsessed with it.
This is so fucking good. I mean this seriously. He's right - that is some Pure Art Skill.
I just love the way art is employed as a necessary component of his character arc. It's so neat. You don't see visual cues that intricate too often. Usually it's just in character design, but watching his entire art style and even his medium of choice change several times over is fascinating. You can really tell Hussie had a lot of fun with him. He's also just really, really fucking funny. Just about every sentence that comes out of his mouth is Grade A Absolute Fucking Gold, and I'm honestly obsessed with his dynamic with Dirk. This may get me thrown to the wolves, but I personally think Dirk and Caliborn have way more chemistry than Dirk and Jake. Maybe that's because we actually see Dirk and Caliborn interact on screen... Lmao.
Necessary Topic: I don't know why people hate him so much. Like, I understand hating his misogyny and fatphobia, sure, but those are deliberate character points and not just Hussie-isms. I see people act like Caliborn is indicative of Hussie, as if Homestuck-era Hussie wasn't, like, famously really fucking good at writing female characters and absolutely not a misogynist. Caliborn's a parody of Homestuck Anti-Fans - which is a term we really ought to bring back, god, anti-fans are absolutely still a thing and good lord they're everywhere - who really were just shitty little bigoted haters. Calliope, the opposite side of his coin, was representative of, essentially, "the best kind of Homestuck fan" - an ultimately sweet young teen girl who willingly dedicates almost all of her time to this piece of fiction she loves so, so much, who draws a lot of fan art for the joy of it all, has OCs that don't fit any of the design conventions in Homestuck whom she pairs with the characters in it for innocent fun. Someone who has a lot of theories and analyses, writes a lot of fanfic, and is genuinely just having a lot of fun. Everyone loves Calliope. Even the characters in Homestuck love Calliope. They just think she's the cutest, sweetest little thing they ever did see. Caliborn was the worst kind. He sucks on purpose. No one likes him. He is a total nuisance to characters he is by all means trying to impress. I love them both.
It's also just funny that he's a canonical Intersex Transmasc who is probably Gay and this has, like, no relevance to anything about him, really. So no one really talks about it. Gender Hilarious, Gender Nefarious.