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My friend actually prefers the older MSPaint Adventures stories with their user-suggested silliness. He got two thirds of the way through Problem Sleuth before he decided that the stories were too up their own ass in snarled, convoluted plotlines for his taste. On the other hand, Homestuck's grandiose multimedia presentation has grown on me with its seamlessly blending the Wagnerian ideal of a gesamtkunstwerk with everything awesome and loathsome about the Internet. While I generally have a low tolerance for most fanbases' bullshit, it's actually to Homestuck's advantage to have many passionate vocal fans to discuss, explain, extrapolate, and speculate about it because it is such a multifaceted story packed with detail. ("Packed with detail" seems a weird phrase to use about a comic that deliberately aims for a more lo-fi aesthetic, yet the writing makes up for it.)
Of course, the author has remained deliberately vague and open-ended with what he'll do next when Homestuck reaches its conclusion, but if I had my way, I'd like to see a return to the simpler, goofier style with more user-submitted ideas on the MSPaint Adventures site but with a more intensive, serious, large-scale story getting its own website. Both approaches have been equally entertaining to me, so I wouldn't mind seeing more of both.