Just for sake of another person's experience:

I did emacs org-mode for over a year and ended up abandoning it. For me, the issue was: I could absolutely see how powerful it could get, but not only was the learning curve wildly steep -- the way it does things is so different from most other programs that it would slow me down in those.

I ended up falling back to a mix of things like zim-wiki, xbindkeys and a bunch of zenity/fzf based shell scripts to get what I wanted, while having something that played nice with everything else, interface wise.