Precise, in-depth video showing exactly how the Season Unending negotiation works, including how it is affected by the progress of the Civil War questline. All possible options, remarks based on options chosen, under what conditions remarks are made, e.t.c..
In brief, many of the factors affecting how the negotiations proceed depend on a “scale” that gets maintained, and points are added to either side of this scale when the Dragonborn makes various decisions. Whenever points get added to this scale, I show a number on the side of the video, the left side when the points are added to the Imperials' side of the scale (as they sit on the left side of the table), and the right side when the points are added to the Stormcloaks' side of the scale.
This gets more complicated if significant progress has been made in the Civil War. If Riften/Markarth has been taken, then the side winning in the war will start out with 1 additional point on their side of the scale. If all Holds bar Windhelm/Solitude have been taken, then the winning side starts ahead by 2 points. However, certain events don’t take this “starting offset” into account, and instead depend on how many points the Dragonborn has given to a side, rather than the current state of the scale.
It is possible to start the Season Unending negotiation when one side only has their base Hold left (Windhelm/Solitude), though it requires some careful timing with quest progression. I’ve uploaded a separate video guide showing how to do this, with a written explanation in the description — ‹//youtu.be/hEvjKPCkO-s›.
For those interested in learning more about how the negotiation works, there’s a guide I have on GameFAQs on the subject, though parts of it aren’t an easy read (I need to update it sometime). I’ve also uncovered a few additional things while making this video, that aren’t mentioned in that guide.

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