Please keep in mind that this country is enormous. I'd hate for you to spend the whole trip in the car. If you look at the driving times on a map you'll get the idea, for example NYC to Southern Indiana is at least 12 hours.
If you will spend most of your time in the middle of the country, I might suggest taking an additional flight to Chicago or Indianapolis and then renting a car there. You could then make a big loop through the midwest and south and fly out again from Chicago or take another one-way flight from some destination down the road and return the car there.
Something like this (http://bit.ly/17Rdsy6) would allow you to see a lot of PondBossers.
