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Quarter Life Crisis?

I am a fan of John Allison -- I've been reading Bobbins-Scary Go Round since literally within days of Day 1 online.  So I was curious to read the discussion on his blog about his thinking aloud about his current webcomic and possible permutations of it.  And I suppose the question of broader interest is -- what kind of things take a quality webcomic (which SGR clearly is by leaps and bounds) to that higher xkcd/questionable content/pvp levels of success?

(John's initial post titled State of the Onion is here, and a follow up post from today is here.)