This was a full page, mostly black-and-white webcomic.
It followed a kid who was in high school and up as he got into college. Had the whole "dark and extremely depressed" thing going on. It was primarily a B&W with occasional colored strips, had a few guest artists here and there (one was I believe by the "Road Waffles" artist, others fail to come to mind at the moment). It occasionally used cigarette smoke as the "flashback smoke" or esoteric framing for telling stories. At one point while still in high school, the protagonist gets attacked by the antagonist. There was a scene with a girl falling through ice and him pulling her out of the water. Eventually, the protagonist has to shoot the bully in the head, and thinks he killed him. Later they end up graduating and going to college and his crush becomes his girlfriend. When they hit college, they run into the protagonist's brother who's getting a degree as a programmer or something and is heavily addicted to drugs. He has a jaunty attitude, is very skinny, and is seen in hotpants a few times (they were pretty comical moments, so they stuck in my memory). At one point the older brother pets his little brother and says, "Sooooooft!," before throwing up in the next frame. Another time he's running around and shouts "Yeeeeaaah, TOAST!" A bit further down the story line, he finds out his bully is released from jail, and the bully now has a demonic-looking dead eye (stylized by being black and smoking as if still freshly shot), and he gets a physique that is somewhat towering and monstrous in relation to his perception of him. Once finding out the guy survived, he ends up having to kill him for good.
They have a squared-jaw looking style, thick inking for the lines, and was very thematically deep.
I am absolutely butchering this, and may even be butchering the series of events (who knows, maybe he didn't end up shooting him in the eye at first and that came later?), but it's been about a decade since I last read this and I was hoping someone could help me remember more details about it or happened to remember the name of the webcomic. I also believe he had just moved to the area his Senior year of high school, but I honestly can barely remember that, either! I've been trying to remember a good deal of the comics I used to read, and I'm afraid I might start mixing them up, so here's to the first step on memory lane *clink* Aaanyway, thanks for your time! ANY help here would be appreciated.