This is a wonderful post Ben, thanks you.  It speaks, to me as a primary teacher, to more than just EdTech and startUps. The big internet beasts have some claws in education and seem to be working towards what you call the  rat-maze simulation of intimacy. Governments seem bent on datafication.

Technology can be part of informal & formal personal relationships. The technology I find interesting is messy engaging and has not much to do with scalability & market share.

In my tiny world, I hope technology helps inclusion, engagement, diversification of approaches and fun. The presentation & recording of learning in a useful way by learner that is still individual, not auto analysable and open to conversation.