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I don't really understand this "to do" list; do we have to follow it in order to progress the story? I'm trying to pursue Rune's route, but in the "To do" list, it says to "spend afternoon with Max". If I ignore it and don't do it right away, will I be able to progress with the story?

When you were first given the Mid-Afternoon scenes choice, you got an information that none of the content in Shelter is missable. That's true. TO DO simply shows you what content you haven't seen yet, and you should just do it in whatever order you want.
Don't treat it like something you have to "win". Just explore it.

Thank you for explaining!