I hope it goes without saying: thank you very much for your contribution to the world, generally.
One way to think about this in the larger sense is that "an interesting person is one who is interesting whether you agree with them or not". This also goes for books. (This is the "it's about perspectives, not about relevance" point of view.)
It's worth it to try to understand what "interesting people" have thought -- it provides context for one's own thinking.
This is eventually the main reason why I mentioned Bateson's work in particular (besides the depth and orthogonality of his ideas).
I've read Watzlawick's work on interaction and pragmatics of communication before I've read Bateson's. I found Watzlawick's ideas easier to grasp (at least, I'm under that illusion), clearly presented with e.g. axioms. Then I read Bateson's work, and got this strange feeling of dwelling around the same underlying concepts, but without a clear understanding of his main argument.
I've read "Steps to an Ecology of Mind" quite a few times (I still re-read some chapters every once in a while) and always felt that a) I'm reading new material; and b) I'm not getting it all. Yet, I always get something new, and this is an extremely interesting insight on how my own perception changes over time.
Of course, this happens with other books and authors. Still, personally, I have a clear feeling that not to the same extent as it happens with Bateson's ideas. It's my own mirror, so to speak.
Having that audience in mind, wouldn't Manuel Castells' work (mostly, the "The Information Age" trilogy) be a good reference? Probably a little too vast.
I think it might be too long for the intended purpose (maybe a little too academic?). On the other hand Mumford also wrote a trilogy "Technics and Civilization" that I did hope they would read ...
And certainly the McLuhan books are more cryptic for most readers. On the other hand ...
Thinking about it, from a practical perspective, I'd eventually suggest "The Internet Galaxy: Reflections on the Internet, Business, and Society" instead of the trilogy. It should be more readable, definitely smaller, while still addressing most important concepts (for me, it was the spatial configuration in the information society: the space of flows).
This prejudice is part of a larger one (which is partly a generalization) that it is rare when commentators -- whether philosophers of science or other -- come close to having a good view. Of course, so many in fields are also quite blind to what is going on. Still, most of the good commentaries I know on science are by scientists, and most of the good commentaries on computing are by computerists. And music ... etc.
My perspective on Castells is biased because it was essentially the backbone of my academic training. I had teachers telling us explicitly that Castells' notion of information society was the framework (in the Kuhnian sense) on which we'd build upon. Having that in mind, I see Castells as a sociologist and his work (sociological) as a view on a society defined by information flows (not exactly computing, although computing and telecommunications are key enablers). Still, he keeps technological determinism at bay by considering the impact of geography, territory, matter - the physical (tangible?) dimension.
What I like quite much about his work is exactly this aspect: he presents a vision of a society dominated by the intangible, while still dedicating rather extensive chapters on the geographical asymmetries of the world. This avoidance of technological determinism, the "information is key but place and physicality still matter a lot, as evidenced by real-world data" notion is why I see Castells as a great reference.
_The Laws of Form_ by George Spencer Brown,
Anything about logic by Gotthard Günther :) (He's a rare bird.)
_Autopoiesis and Cognition: the Realization of the Living_ by Maturana and Varela
Anything by Niklass Luhmann about social systems: the economy, mass media, art, functional differentiation, … He was a student of Talcott Parsons
Norbert Wiener, _Cybernetics: Or Control And Communication in the Animal and the Machine_ and _The Human Use of Human Beings: Cybernetics and Society_
_An Introduction to Cybernetics_ by W. Ross Ashby
McCullogh and Pitts (You mention Minsky but not these dudes.) _A Logical Calculus of the Ideas Immanent in Nervous Activity_
Basically, most of https://en.wikipedia.org/wiki/Cyberneticist
? :)
A lot of the books you mention were listed in the Whole Earth Catalog, and were favorites at PARC.
Especially "Laws of Form".
And some of the other "Cybernetics" circle books (Bateson et al was part of the Macy Conferences on Cybernetics, etc.) Both Maturana and Varela were around in those times as well.
Minsky was a huge fan of Warren McCullogh and Walter Pitts.