I do 50/50 driving, by distance, every day. The 50 in town takes 5x as long as the 50 on the highway, and averages a dozen stop/starts. There is a long hill on the highway to boot. Lighter weight will win every time.
I'd assume the bigger car would need a bigger engine too, so it would have a hell of a time catching up to the lighter. Would need to be 1:2 ratio or higher to ever make it worth it. And, as point out, aero can be worked on...you'll never be able to take 1000lbs out of the bigger car, and it would be a pain to shrink the engine size.
All of this assuming a plain old gasser. Hybrid or diesel and things would narrow a fair bit. Also gotta assume the heavier car can carry more (people) and be more comfortable. I rather like a comfortable ride...it's worth a few bucks a week in extra fuel.
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