The only "joke" I've had in my town was to put the Church in the middle of a lake, so people going to and and from have to walk across water to get to it.
My whole Sprngfield is an inside joke with the entire town cut off from the world except for Frink, every building is its own island, essentially a giant moat around the town. Frink's place is essentially running an experiment. Admittedly I have 20 brown houses and now the prison at the top by the mountains but I am looking at those as a naturally inaccessible path. The brown houses I see either as row houses or in my deeper inside joke it is all set up as a version of The Prisoner where those are houses of people that work for the organization as control.
Nothing anyone would really see, but it makes e laugh.
Also I put Willies shack in a park/forest area kind of as a secluded wacko type.
I put the retirement house next to the cemetery and a mausoleum next to the retirement house, but I think that is pretty obvious.
I love seeing the other funny things people do and LOVE the church across the water, too funny.
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