You can't figure out what state they are coming from based on clues (I know, I tried)
While driving to Orlando, Skinner passes a sign for Orlando 2653 miles. The closest to that figure would be Springfield, Oregon at 3200 miles. OK, MAYBE he took off and saw the sign 300+ miles down the road. But that means he still drove the whole thing in ....what.... one day?
Humor always dies on the operating table You can't dissect it