Reminds me of an article I saw sometime back on HN: "Manual work is a bug" (https://queue.acm.org/detail.cfm?id=3197520). Just like you, the author's advice is to go iteratively, with the first step being documentation. As documentation improves you act more as a cpu running instructions, at which points automation becomes clearer, and so on. Not everything can or should be automated, but we definitely could do more.