I like the idea of a faction controlling the road.
But they can't be completely evil, they should be potential friends.
Also i think the shuttle should be a death machine.
Turn it on and it will allow safe travel between Seattle and Portland for passengers, however this will also bring the destruction of several toll post built be the faction mentioned before, thus crippling trade for that faction and ruining your reputation with them.
A game like Fallout should be filled with morally ambiguous choices.
And yes there must be funny hats!