I have worked with machine vision and currently I'm doing my PhD in computational logistics (mainly working on automating the deployment of Vehicle Routing Systems). With this background in mind have given some tought to this: What would be needed, at least in the transition phase, is technology that would allow remote drive-by-wire of trucks in difficult situations (platforms, urban traffic) and wheater conditions.
Imagine a system not entirely unlike the unmanned UAVs the US is using but for civilian use of remote controlling trucks. One driver could probably handle dowzen or so trucks because they would drive under full automation at least 90% of the time. In addition the truck driver could have a normal 9 to 5 job.
Of course there are technical challenges like communications delay etc., but I'd like to hear your opinion on feasibility of such system.