Car makers would adjust but road freight would fight this tooth and nail
Last mile I will give you. Those shippers use trailers and containers on railroad cars, and trucks do the last mile delivery.
I'm sure it's pure coincidence that many cities already have rail lines going down roads in city centers. They probably just built the city around a historical freight line, and haven't bothered to remove it.
but maybe this would just incentivise the sort of person that buys an F150 to drive to the shops to simply to upgrade to a big rig (for the tax saving?!)
No, you just have to charge in proportion to damage done and let the economics work out how they will.