Great list there, I’ve fortunately managed to see about 25% of the episodes listed there. I’d probably still swap around some of the episodes so there’s a stronger lead-up to “Behind The Laughter”, maybe “The Cartridge Family” before it, and I’d probably shift “City of New York Vs Homer Simpson” in there too as a penultimate episode, since the car gets totalled.
For the “Sexy Flanders” scene, maybe we could edit in a brief sub-plot for the Simpsons where they find Ned on the slope and him fitting into the jumpsuit is one of his ways of ‘coping’ with Maude’s death?