Although the paperwork problem will definitely be an under-appreciated obstacle to making these systems work, autonomous trucks will eliminate a significant portion of it because there will no longer be any such thing as hours of service, or mileage logging for drivers.

Ditto for licenses, drug tests, background checks, and most of the common kinds of moving violations. and scheduling has its own set of paperwork which is a colossal nightmare because you are dealing with the always conflicting priorities of drivers on one side and customers on the other.

The major logistical obstacle outside of paperwork will remain to be resolving last-mile issues, but that has already been resolved long ago for containerized railroad freight: a.k.a. autonomous trucking technology from the 1800s. There's been a century's worth of time to solve this, manifested in the form of short-haul service providers known as intermodal draymen who pick up the container from a designated landing area (a rail yard) and haul it the last mile. This can easily be adapted to autonomous trucking logistics.