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Crossposter progress update: Optimal splitting into threads works! It was a big one. Turns out I need dynamic programming to find the optimal splitting points in a thread. What does an optimal splitting point mean?

Try to split on paragraph boundaries, then on sentence boundaries, then on commas, etc., then inside a sentence. But never split inside links, images. And make sure the last segment is still a meaningful post, not just a leftover fragment.

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o3 was super helpful in the dynamic programming part. I also added manual splitting hints, using ---. Now, if I insert ---, I can force a split so that an image appears in the first post, for example.