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Don't you think it's a better option to do this order?
- TJ first, it barely has supernatural, it's the most chill and is good for "beginners"
- Then Carl's because it's kinda "separated" from the rest of the story and has a good horror ladder.
- Then Leo's, probably the scariest, introducing new elements to the story, but just briefly

- Then Jenna's, telling you even more about these elements introduced in Leo's story (also the dam scene is so good)

- Then Flynn, because it's the most complex, scariest (Sydney's flashbakcs), saddest, most wtf, and mostly because the very end of the route is like a twist: Within a few lines, you understand everything about the story, the past, the *truth*.

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I Think you could easily change places among Jenna and Flynn's route. I could tell Jenna's is the canonic good ending and Flynn is the canonic bad ending.