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Notes -
Can you compare Obsidian to org mode specifically? Org seems to have a lot of the advantages you highlight, and IME, the Org people aren't nearly as insane as, say, the OpenBSD people when it comes to egoistical free software BS. What specifically would I miss by sticking with Org?
I just don't want to touch emacs with a ten-foot pole. Last I tried, even the most «user-friendly» setups of Emacs+org-mode felt flaky, slow to start, and plain ugly – bad at handling multimedia, bad at rendering, bad even at smooth scrolling, with a lot of dicking around .emacs to get anything done well. It was clear that I need to dig into Emacs Lisp and build my tools from the ground up. I also don't like the concept of buffers and frames as separate from tabs and windows; it makes sense in the context of programming, but I seriously don't need an IDE in a pure note-taking tool.
If you like emacs, you definitely should use org mode. It is conceptually elegant and of course open source. Even core features of org mode like the agenda view are very good, AFAIK impossible to replicate in Obsidian (to some extent possible in Notion), and I know that's only scratching the surface.
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