Doesn’t this assume that the cost will not effect behavior? If trucking logistics becomes more expensive to properly account for the externalities, wouldn’t companies be more motivated to find more cost efficient methods. I’m sure there are plenty of items that could be shipped by rail, but aren’t because trucking is currently cheaper for the individual company, while the cost in road damage, pollution, greenhouse gasses, increased traffic, etc. are paid by everyone else.
As for disproportionately affecting the poor, sales taxes (like on groceries and other goods) and excise taxes (like on gas) are exactly the regressive taxation systems that burden the very people living paycheck to paycheck. Shifting the tax burden from skimming off the top for the people spending all their income on daily necessities, towards companies paying the full cost of their chosen operations, would give the poor more buying power and allow market forces to find and utilize the most effective and efficient means to provide services instead of the cheapest means that are only cheap because they are subsidized by everyone else.