Well, it ain't gonna happen. Not to be a naysayer because I dig your gumption, but there's way too many stumbling blocks preventing this from working out.
1) Indiana + winter = fuel mileage falls off. I hate how much my mileage fades in winter and I'm just in TN where we sometimes hit mid-50 daytime highs in winter, your conditions are going to be worse.
2) Automatic. Yipes. I found a PDF that goes pretty in-depth into the F-4EAT in your car but I'm typing on a Kindle right now and the idiot thing won't let me paste the link. I'll come back later and patch that in. I'm thinking about a TC lockup switch that would command lockups at will, pick up a few efficiency points earlier as you're pulling away from lights. Say, get it up to 2nd and command the lockup. I'm wondering if you could also jigger the shift points at all. I don't know, I just found the doc; I haven't read it yet.
I think your best chance of winning the wager is the lowest speed you can find that will satisfy the conditions of the bet, and try to run it all with the prevailing winds. Aero mods will help. But since it's a friendly wager, I think you're going to wind up owing your friend a pizza (or whatever).
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Lead or follow. Either is fine.
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