I build developer tools and services at Microsoft (currently Codespaces, Live Share, IntelliCode) and maintain some OSS projects (CodeTour, GistPad, CodeSwing, WikiLens)
I'm not sure if this is exactly what you had in mind, but I just released a new extension this morning (called Code Tour), that allows you to record and playback interactive walkthroughs of a codebase. Might be interesting for your use case?
I feel like the process of learning codebases should be more guided, interactive, and integrated into your editor. Not buried in documentation. To improve onboarding, and make it easy to create such learning assets, I created a "tutorial recorder" for @code. It's called Code Tour
15:19 PM - 08 Mar 2020
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I'm not sure if this is exactly what you had in mind, but I just released a new extension this morning (called Code Tour), that allows you to record and playback interactive walkthroughs of a codebase. Might be interesting for your use case?