I can feel this deeply because even though I'm an Emacs user, and thoroughly like the Emacs + Org experience, I was never able to keep a working system organize

I can feel this deeply because even though I'm an Emacs user, and thoroughly like the Emacs + Org experience, I was never able to keep a working system organized with Org mode. I ended up using OmniFocus for my tasks and Notion for "information and note storing"; they have great, built-in support for the things I need to do and I spend very little time managing them and keeping them in order, so they simply do "what I need them for". They also play nice with mobile devices, images and external documents, and integrate with my Outlook calendar (something I am forced to use for work). I have no doubt that a proficient Emacs user could create something similar, even better, using only Org mode; I don't use third party configurations and keep mine to one hundred lines, more or less; when things get more complicated, I notice that I mostly end up in a game of min/maxing without getting the same amount of "useful" that I get from other systems. The big problem is that, the way I'm running now, I don't own my data; OmniFocus worries me particularly because, as already said in other comments, it's Apple-only. Notion worries me too: I wish them all the best, but what happens if they go out of business? Sure, I can export everything in plain text, but the structure of my data would be pretty hard to recreate in another system. Even though configuration + Org files amount to some amount of complexity, I can have trust that their format is long lived and that they are stored where I decide. This is a sort of "peace of mind" I can relate with, and that I have somehow lost when I decided to use these other systems; however I am infinitely more satisfied with two systems that do "exactly what I want"; I hope to find a way to reconcile these ends sometimes, but for the moment Org mode is "only" my outlining tool of choice.