thank you for this ! I planned to do the civil war right away but neglected to do much of anything else, and felt that a 20 day delay wouldn't have been enough time to get to a cornered rat and finish the college
I haven't found any way in which Timing is Everything interacts with Second Great War? If the only way it does that is that TiE changes the timing of prerequisite quests for SGW then it should work fine.
What this does is make the quest that causes the courier to show up in the first place only be triggerable after either the quest to kill Astrid at the very start is completed (in the shack) or when "Hail Sithis!" is complete, and it identifies those quests based on their internal ID in the game. Assuming the Your Choices Matter edits keep those quest IDs (rather than, say, replacing them with new quests that have the same name but different IDs), they should be compatible. I do not know if that's the case, though.
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