No Kolmogorov complexity -- the course was really a history from Hume to about 1970. The next time I teach a seminar, I'm hoping to cover 1970 to the present. Still, this time around, a lot of the readings were technical: Ramsey, Jeffreys, Fisher, Neyman, De Finetti, Savage, Carnap, and others. You can see the full reading list here.
I agree that a nice course on progress could be done with a philosophy of psychology focus. I expect that progress-skeptics would object that the progress is in psychology itself, not in the philosophy of psychology. (I wouldn't share that skepticism for a couple of reasons.) Maybe if the course were framed more in terms of philosophy of mind and computation? Have you read Glymour's "introduction" to philosophy, Thinking Things Through? It has that feel to me, though it's pitched more like, "Here are things that philosophy has contributed to human knowledge," and it ranges over more than mind and computation.
It's a very interesting suggestion. I haven't really taught history of philosophy --- a big exception being a graduate course on the history of work on the problem of induction from Hume to Quine, which I taught in the spring. Basically all of the courses I've taught are current topics, arguments, and controversies that are live today. Course titles like "Logic and Reasoning," "Biomedical Ethics," "Contemporary Philosophy of Science," "Metaphysics," and "Philosophy of Psychology."
Maybe the way to teach something like this would be under the heading "Progress in Philosophy," where you could sort of split time between  the contemporary debate about what counts as progress and whether there is or could be progress in philosophy and  some historical examples. (This was also a major theme of the grad course I taught in the spring, so it's still very much on my mind.)