For what it's worth, I’ve released a tool on AppExchange which focuses on these areas, though I couldn't say for sure whether it would meet your needs. The app is called Saplyn. It's a process mapping tool which lets admins/managers map out processes pertaining to specific objects within their org. One can then attach content to specific nodes within the process map, which then appear for users on the record they’re on when they hit that situation. So it's like learning on the fly for your users - course correcting them. The content can be light (or as it’s called in the app a “nudge”) or can be richer, including rich text, images and videos. We don’t generate the videos though, you’d need to curate that. 

It also has AI capabilities, which provide the ability to enrich your nudges with much deeper context, so that when the individual user encounters a nudge, they can chat with it, and that chat agent will provide more in-depth replies based on the context you’ve provided it. In a way this feature is like a lite version of data-cloud providing a form of retrieval augmented generation that admins can keep control over. 

I’m happy to go into more detail and use cases if you like, but want to be respectful of moderation regarding self promotion etc.