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One reason we don't have more interesting, quality structured text editors: it's *really* hard to implement table-stakes editing operations well, particularly on web. In this video, I attempt to arrow up/down and shift+up/down to select inter-line in 8 outliners. Very yikes.
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I’ve been exploring the approach of using pure plaintext but augmenting it with some controls in the margin. Because I know I can’t re-implement text editing to my own standards. I feel like this can be taken pretty far. My work so far: tasktxt.com
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Incidentally, is there a name for this paradigm? I've been calling it "decorated plaintext"—the aspiration to the core editing interactions and data fluidity of plaintext editors, but with some of the higher-level semantics/affordances of structured block editors.
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You're right about long items, my solution would be to break things up into something like pages sooner rather than later. I'd like the barrier for doing that to be as low as possible. I'd really like to further explore a design-tool like canvas for organizing text.
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(The sibling-paragraph issue has been relevant for me exploring a textual canvas for question/answer pairs… for shorter prompts, "Foo bar? Baz." works pretty well as a one-liner syntax, but I don't think I can get away with it in general, alas)