Ever since I've first learned about his story in-depth, this idea has also fascinated me – but I've never seen anybody else raise it unprompted!
The analogy with software is right-on, in my view. He crated a system that was complex, sure, but very manageable and powerful if you understood it in sufficient detail.
For a fast-and-loose comparison, he was running foreign policy in Vim/Emacs, while his contemporaries were using Notepad, and of course he did a damned good job. His biggest fault is that he never taught any of his subordinates how to use Vim/Emacs.
He didn't seem to have a succession plan for himself. It's a mystery to me why (hubris, lack of interest?), but it regardless goes down as a fault against him, IMO.