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Short answer: because Marcy Lowell is such a bitch.So the question is... Which is your favorite playset? What makes it a better playset than all others?
Longer answer: I've actually never played Main Street, but I have played Tales from Suburbia. And it was a good game. But those playsets felt a little bit more generic. Flyover has a little more material in there to spur on the imagination. The flyover playset has little narrative threads that run through the various elements, that let you take them and build things. So Marcy Lowell shows up in a lot of games of Flyover, and she's always terrible in beautiful, awful ways. And the airport is always involved in smuggling or drug dealing or something. Or the Mexican drug dealers and the tear stained letter written in badly broken Spanish...
Flyover also gives you a small town setting. Everyone knows each other, at least a little. The small town setting means that there's plenty of isolated spots and abandoned run down barns to hide your meth labs in. But it's not the crazy isolation of The Ice (another great playset), so you can still go into town and have a shootout in the community health center or whatever. I can picture Flyover country in my head and spin out cool specific details real quickly and easily without them feeling like I'm just using stock, generic settings.
Of course, Flyover is also the first playset that I played, so maybe it's a mental reaction to the discovery of something new. It's also the playset I've played the most (five or six times at least) which may also relate to my liking it.
Flyover has never failed to give me a great setup and an entertaining game.