My experience with Homestuck seems to be opposite most people's.
I thought it was really weird and kind of boring at first (probably first 100 pages) , but once they started Sburb I thought it was pretty funny. I enjoyed it more and more for a while, but then everything just felt like it was getting really convoluted and the story seemed unnecessarily complicated. If a story needs to have an author blogging and answering questions so people can understand what's going on, I don't think that's very good story telling.
I know I'm in the minority here. Homestuck is an incredibly impressive work of art, but I find it difficult to enjoy it.
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No amount of planning will ever replace dumb luck.