The quest that leads to building Skip’s Diner begins straight after Miranda Rights concludes, when Wiggum has done his second Springfield patrol. It begins level 18 in your regular gameplay (although I well beyond this on my XP bar due to playing the game and visiting friends – but that’s perfectly normal, so don’t worry if this happens to you!).

Homer and Comic Book Guy should have been free as Chief Wiggum finished Miranda Rights Part 4 (while Marge isn’t really needed, keep her free as well to be safe):

1. The Only Sport America Still Dominates Something’s happening at Krusty Burger that’s got Homer excited:

Homer: I’m gonna win it!
Marge: If we lived somewhere else, you’d be a shoe-in. But Springfield is the obese-est American town not in Mississippi!
Homer: I couldn’t live with myself if I didn’t try!
The hamburger-eating contest begins and Homer, Comic Book Guy, and Chief Wiggum all enter. Comic Book Guy and Wiggum eat at the Krusty Burger 4 times and Homer eats there 5 times to complete this quest (each visit goes for 30 minutes – keep Comic Book Guy free as Homer finishes his final visit):

Naturally, Homer beats out Chief Wiggum and Comic Book Guy and wins the grand prize – five more Krusty Burgers!
2. As American as Apple Pie Part 1 Comic Book Guy is still hungry, though and goes to eat at Krusty Burger one more time (30 minutes)
3. As American as Apple Pie Part 2 Still hungry, Comic Book Guy goes to Gulp ‘n’ Blow to satisfy his superhero-like super-appetite (60 minutes)
4. As American as Apple Pie Part 3 Still hungry and convinced that Springfield needs somewhere classy to eat, Comic Book Guy prompts the build of Skip’s Diner ($35,500 and 24 hours)
5. As American as Apple Pie Part 4 Satisfied, and comparing Skip’s to that diner in the monie “Diner”, where everyone dined at a diner, Comic Book Guy goes to dine at Skip’s Diner (4 hours and apparently the Worst. Quest. Ever. Keep Homer free as he finishes)
6. It’s A-Me-Luigi! Despite all the hamburger eating, Homer’s in the mood for pizza – as long as he doesn’t have to build anything. That’s the cue to begin the Luigi’s build ($51,000 and 24 hours, unlocking Luigi when the build finishes)