This is total conjecture but I can imagine him doing something like this: Question: how do you make students the most miserable? Answer: create a dorm that discourages social interaction, and is far from classes and amenities.
Starting from that, you do the opposite: create a large, centrally located dorm where the design discourages sitting in your room and encourages use of shared spaces while benefiting from greater density and central location.
If the question is "are windowless rooms good?" the answer is "no." If the question is "are we willing to sacrifice bedroom windows so that we have grater communal life and better walkability" the answer is probably "yes, possibly."
Logically it's the same argument for why some people prefer to live in small city apartments when they could live in a much larger home elsewhere for the same price. The very nature of city real estate is tied to the nature of city life (both as a cause as an affect) and it's simply a tradeoff. Asked on its own "do you want a cramped apartment" the answer is always "no" yet people often opt for it in context.