So I started following Homestuck four years back, at the start of high school for me, and sometime in 10th or 11th grade, I didn't keep up with it anymore. I've collected bits and pieces by all the posts in-tag, since I can't remember exactly where I left off. My question posed though is: should I feel bad for not understanding so much? For example, I don't understand jujus and their functions even though I was still reading when they were first mentioned... I just feel bad for not understanding

Dude it’s a story, a piece of fiction, like there is no problem in not knowing literally everything about it. Plenty of people don’t understand how things work or what they are in homestuck, explaining that shit is like 95% of what this blog does. So no, you shouldn’t feel bad.