The geometry- and mechanically- related tasks seem like they would be ripe for automation. For example, the trailer reversing problem is related to the inverted pendulum problem, which is easily solvable by automated systems.

The judgement for when to stop with an unsafe load and wayfinding at the last 100 yards of a route are indeed tasks that I'd prefer to leave to a human for the time being. Maybe we'll have 'dock pilots' like we do for large cargo ships?