I think the trick with Emacs and Org is to stick to the basics and then only add features or change your configuration very slowly, as needed. I have been using Emacs non-stop for >20 years and my .emacs is just 20 LOC. It's been shrinking, not growing. My goal is to bring it down towards 0 LOC. I have committed a few things upstream to modernize defaults.
Personally, I think the reputation of Org, Emacs, or Nix being hard and complex is undeserved. It's rather a documentation problem. There's no simple documentation to onboard newcomers and show them the basics in a principled way. So it looks like a mess, but it isn't.