I've been playing around with a similar problem 'Can AI help me increase my literacy around Art & Design' but have taken a bit of a different approach, essentially:
1. Have a rough rubric around areas of knowledge and where I'm strong/weak
2. Every day an agent builds a ~30min task + short answer question and slacks it to me. Tasks are designed to have minimal AI writing and pull primary sources / courseware. Easy to do in downtime or during my commute.
3. Answers are picked up from Slack, are scored against the rubric, and progress is tracked day over day which influences the task for the next day.
Stack is dead simple, scheduled Claude Cowork task + state in Obsidian + Slack for messaging. Happy to share more details if people are interested but easy to replicate from the above.
One of the things it's opened my eyes up to is the sheer volume of high quality works/analysis/videos/courseware available online. You really don't need AI to process this, but it's helpful to have a wrapper that identifies/points you to the resources that will be the most helpful for you.