At the moment I have done 0 Civil War Quests, so Jarl Balgruuf still controls Whiterun. Here Ulfric demands Markarth, you can give the Empire the Rift of the Pale, Ulfric has to pay his massacre at Karthwasten, and Ulfric demands Falkreath.

Assuming I was a Stormcloak and took over Whiterun, Falkreath, Dawnstar, and Markarth, what would be the case then? Would Ulfric demand anything? Would he have to compensate for Karthwasten? Or would Tullius demand a hold, and would he have to compensate for anything?

Assuming I was a Legionnaire and took over all Stormcloak territories EXCEPT Windhelm, what would Ulfric/Tullius demand then? Would either of them have to pay compensation for a massacre?

This was my favorite quest of the entire game. I have a save file in case I ever want to replay it.

I think you have to do the Season Unending quest first in order to begin the battle for Whiterun. That means that there isn't really another outcome.

That's wrong CaptainG, the Battle of Whiterun can be completed before or after Season Unending. It's all a matter of when you do the Civil War or the Main Quest.

This should serve you well.

http://www.uesp.net/wiki/Skyrim:Season_Unending

I'm normative neutral during the MQ and and leave Season Unending as a neutral treaty. That said, because of the way the system works, the Stormcloaks get an extra hold.

It's possible to be neutral in SU?

I always get a result of Ulfric being pissed or Tullius being pissed, and Balgruuf always gets mad about Markarth.

You couldn't. The Stormcloaks have no territory to offer, and the Imperials would be wondering why you'd be wasting time when victory is so close.

Basically, just finish the job and be done with it. That way, you can make Ulfric see the ultimate cost of his rebellion by having to personally pay it himself.

If the Stormcloaks control Whiterun, Tullius starts out the negotiation by demanding the Rift. Whoever is in control of Whiterun (which by default is the imperials) is in stronger strategic position, so the other side tries to even the playing field before they'll talk about a truce.

Didn't knew that, thanks for correcting me.

You can.

Something among the lines of:

Elenwen stays (1 point Empire)
Riften is traded for Markarth (2 points for the Empire and SC)
Because Elenwen stays, you give Morthal to the Stormcloaks (1 point to SC)

2+1=3=2+1

Makes sense. Thanks. Will do this instead.

I like the way Stormcloaks look and what they fight for, but I dislike Ulfric.

Also I like Balgruuf and I HATE Vignar.

In the end I mostly choose Imperial, but I prefer staying out of it.

Always meant to try this but what would happen if I try to do Season Unending after taking Morthal? Stormcloaks would have 8 of the 9 holds, would I need to choose to make the Empire pay compensation for something?

If your side already controls eight of nine holds, then the Jarl of Whiterun feels secure enough to let you proceed to "The Fallen" without needing to complete "Season Unending".

It's possible to play the system to get more territory for the side you favor. For example, by telling Elenwen to leave and letting the Stromcloaks avoid paying any compensation, you can get an extra minor hold for the Empire -- either Winterhold or Dawnstar. However, the game sees this as a Stormcloak "victory," even though they gave up more land than the Empire.

Strictly speaking, favoring the Stormcloaks is better because any newly-ascended Jarls trust you enough to sell you property, and both minor holds they can obtain offer homesteads with Hearthfire installed whereas only Dawnstar has a steading for the Imperial side.