I find older essays much better than contemporary ones, which is why I currently read Chesterton, Emerson and Montaigne the most. Thanks for this, I'll explore other writers from your list.
For what it's worth, Roam team has just recently added end-to-end encryption option for graphs.
I'm a Roam user, although I've tried Obsidian, Bear, Zettlr and vimwiki. I keep coming back to Roam because I find thinking in blocks suits me better than thinking in documents.
To be fair, just look what happened to Skype after Microsoft let a designer loose on it: https://hn.algolia.com/?dateRange=all&page=0&prefix=true&que... They might have wanted to avoid that and just let their devs dump data into screens without a real design.
I'm not a big fan of what some designers deliver, but sitting down with maybe one or two users and seeing how they try to make sense of the mess that is AWS might have made sense.
I know exactly what you are talking about. After following Ultraworking Lights [1] for a couple of months, everything started feeling mechanical for me. So, I've stopped doing it and instead started doing anything I just feel like doing each day. Which comes with its own set of problems.