Not quite. Long haul trucking has far more things to go wrong than a short jaunt from two packed urban spots to another. A lot goes wrong on these trips. Flat tires, accidents, bad weather and - of course - other drivers.
Case in point: a long haul truck from Oakland to Chicago has to tackle Donner Pass, the Wasatch, Sherman hill (the Wyoming continental divide) and then finally gets a flat stretch across the Great Plains.
I would counter that the best start is short-haul intermodal: trucks that pick up a container and haul it to an intermodal rail yard, and so on. Those trucks have to deal with a short route and much fewer potential problems.