I can’t answer all your questions, but I have a few suggestions. If you lock the camera down in the car, you don’t have to chromakey – you can make a mask instead (easier because it’s not dependent on color).
Have someone drive you through the route and shoot out the window without any of your car showing and at the various angles you will need.
Then show the route footage through mask.
This is easy to visualize but hard to explain.
Good luck,
Mary Waitrovich
UW-Madison