This episode came toward the end of the the 3rd season, which was ramping up for the greatness that is the 4th season. For an episode so packed with excellent writing, it's actually a very simple episode. The plot doesn't take big turns, there aren't side paths that distract from the plot. Homer's B-plot is a wonderful distraction, but never feels like it takes away from the A-plot. In fact, Homer's plot is so brief that it could probably be boiled down to taking up about three or four minutes. But every line in that plot is just fantastic. "There's a Machiavellian countenance." "Lamentably, no. My gastronomic capacity knows no satiety."
Bart and Milhouse haven't had a story with as much emotional resonance as this one. Further adventures usually deal with Milhouse's family life, or focus extensively on how much of a loser he is. That's not to say they aren't entertaining, but this story treats Milhouse in an unusual light. He's ahead of the curve with Bart. Eventually, having a girlfriend would make him much more confident, and Milhouse would easily overtake Bart's dominance. I'm reminded of the relationship between them during Bart Sells His Soul, when Milhouse has ownership of the paper, and Bart is getting frantic.
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