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Hey Matt,
I thought I had an easy solution for you that would have you easily winning here. I reviewed your parameters here and the best I can do is for you start your quest at Hoosier Hill. This is the highest point in Indiana. Admiringly it doesn't say you have to pull this off in Indiana, so I'd fine the highest point to start from and that would get you 60 mpg. Should be easy to win this bet!
Good luck.
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