There's a few easier steps they could take first. Long haul point to point from a few major distribution points to others is probably doable soon especially if they're designed to accommodate the autonomous trucks. Local drivers who are paid less drop off a trailer at a UberFreight depot in Southern California, an automated truck picks it up and drives freeways over to the UberFreight depot for Eastern North Carolina, there another local short haul driver gets booked to take it to it's final destination. Uber might be burning too much money to make it to this but the technology for long haul freeway driving is largely here already it avoids a lot of the difficulties of small roads.