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Two cars would be twice as expensive as one, in terms of insurance, maintainence, and mods. Unless there's a severely extreme mod you want to do to one, like a boattail, 2" of ground clearance, or electric drive, I say do all the mods to one car.
Highway driving is mostly about aero, and city driving is mostly about driving style and weight reduction. Even so, aero tweaks will improve your city FE, and weight reduction has a small impact on your highway FE.
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