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Example from my own writing:

He wouldn't have guessed (that) there would be someone with diarrhea in the toilet. Or that the ferry's rail would be half his size. Or that the night would become dark, windy and rainy, making it impossible for the ferry's crew to find him in the water."

I think the first that is unnecessary. But adding it would make it symmetrical to the other sentences. Is this something that writers usually do? Or I should just omit that first that?

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I agree with both your points: if your first sentence stood alone, I'd omit that. But in sequence with the other two, it sounds better to leave it in.

There is an actual rule in English linguistics called that-deletion, which allows you to drop the word "that" before certain independent clauses if you choose to. In this case, I'd keep it.

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