We describe an ongoing initiative to incorporate generative AI for online higher education classes at a large public U.S. university. Our specific online-only class setting poses special challenges: the technical backgrounds of incoming learners tend to vary widely across domains, making the potential for personalized adaptation especially compelling; the majority of instruction is via pre-recorded video, with some live office hours support and forum discussions, making it critical to promote additional effective engagement and self-assessment. Toward these goals, we describe what we have learned and been thinking about in our early explorations, with an initial framework starting from using generative AI to create questions and other rich metadata from lecture video that can support instructor- and student-facing affordances for learning and discovery.