I really enjoyed reading about your efforts in recording your learnings, specially the part where you talk about connections, as it touched a very dear topic to me.
I’d like to point you to https://spines.me (disclosure: I work there), a learning app that I think you will find useful, or at least, worth investigating. Many of the themes you touch in your essay are the motivation that brought us together to start building Spines.
Please, feel free to delete this comment, as I don’t want it to become an ad for our app. Just trying to help you in your quest.