1) The model most are working toward is "hub to hub" not point to point. As in, A human driver drives the truck from the warehouse or port to a hub on the highway outside the city surface streets. Then they get out of the truck and pick up another one that needs to go back into the city. The truck then drives itself on the highway to another hub near its destination where another human driver completes the trip. This works in multiple ways - it allows human drivers to deal with the hard part of automation while also avoiding the terrible away from home lifestyle, and it allows you to have dedicated autonomous trucks for on-highway separate from your human-driven fleet (you can swap the trailers instead of using the same cab). You'll see these hubs start cropping up in a couple years.
2) On-highway autonomy is not that far away anymore. It's definitely not a "next year" thing, but mid-late decade is a near certainty based on the current state of the tech. That's a long time for people used to software, but not a long time compared to the lifecycle of a truck.
3) There seems to be an implicit assumption in this write-up that autonomous systems will remain horribly expensive, which isn't true. They're expensive today because each generation of development is effectively custom built in small quantities. Just like Starsky said their camera system would drop in price with scale, a "ready for production" generation of autonomous driving kit in a few years will likely be close to 1/3 the current kit cost, which has very large impacts on the total ROI calculation.
I don't want to make it sound like there aren't big challenges left to solve - there are - but there's also a reason so much investment money has flowed into this space. The ROI does make sense, just not on the original hype-cycle timeline that a lot of people reported.