Great idea that I would surely be interested in doing. Luckily for me vacation is never a problem, I get plenty every year and there are no certain times of the year I "can't get away". The only exception would be bringing my wife near the end of September would be very tough as it was this year, when she finally got there at 1:30am Saturday morning.
I really like the back roads ideas, but obviously some interstate may be required.
Not sure if anyone has heard of a similar program called Rally North America, but it is very similar to what Chris is proposing, but on a much larger scale. They have scavenger hunts, location finds, where you have to take a picture of the location to prove you were there!
One year the group came through Clarksville and had organized with our local 1/8th mile drag strip to let every one run down the strip as often as they wanted in the 4-5 hours on site. Then they had to "find" the Jack Daniels Distillery based solely on a picture and no other clues. Anyway, I really like the format and we could incorporate some of the same types of things in ours.
I am ready to do something else besides just the shootout that's for sure!
Smitty