Yes, but suppose there's a "road company" you'd have to pay a toll to. Obviously they love profit margins and since they're a monopoly (they own the road) the toll would soon balloon to $20 then $35 then $100.
I don't really think "Yankee Swap" is the best model for land management, my guy.
You can’t opt out of high taxes.
I highly doubt either any future city government would allow all the highways to be converted to privately owned toll roads.