It's not unlike many college kids taking a job as a security guard and "watching monitors" while doing their homework, etc. (Another thing that I considered, but never actually did.)
Of course, there's a lot more training for truck driving, but I don't see that as a major barrier, given the benefits of extra pay and travel.
1) Automated gears and obstacle detection - we already have this. 2) Have the truck stay in one lane and maintain distance - We're close. This means humans stay in truck and solve the hard problems when encountered. (Kind of like pilots) 3) Automated port to port driving without humans. 4) Destination to destination driving without humans.
We already fly military aircraft remotely, I don't see why a truck that's packed with cameras and sensors can't be driven safely by a human in an office somewhere.