It follows that, say, many with or pursuing a PhD in Machine Learning and related have also picked up a majority of your desired (per your recommendations) philosophical skills

No, I wouldn't say that. The problem is that we (humans) don't know how to teach the philosophical skill I'm talking about, so there aren't classes on it, so I can only recommend courses on "the basics" or "prerequisites." I don't know how to turn a math/CS PhD under Stuart Russell into the next Eliezer Yudkowsky.