He does point out some problems that make technology and societal predictions hard. However, I believe it is possible to be quite accurate.
I agree with him that understanding the past and the past of technology matters.
I agree with him that details and downsides of products and technology matters.
I agree with him that we cannot ignore the infrastructure that exists and how quickly it might be improved or how much investment is needed to keep infrastructure from degrading.
However, I do clearly see technology that is being worked on and developed and which will have a more profound impact on society than Bob believes will happen.