Board Thread:General Discussion/@comment-209.237.126.90-20181213202539/@comment-26213507-20181214021138

Well, the short answer is that they wouldn't. Half of Skyrim supports the Empire, so they'd need to control those people and prevent another uprising with the remnants of the militia they have from the Civil War. It'll take at least ten years to get forces and food up to at least a survivable rate, and even then, it would not be ideal. The countryside is full of bandits, and even though the war has concluded, I doubt Ulfric will do much for a long time, which means that it will indeed be a lawless time everywhere.

He'll also need to secure the Reach from Forsworn if he wants aid from the citizens there, since they directly oppose him since the Markarth Incident. It'll be much harder to hold the Reach as well as Stormcloaks, since the Forsworn preferred the Empire, who didn't burst into Markarth and decapitate any who would not listen to Ulfric's militia.

All of that is just internal. They'd have to then secure Morrowind or Cyrodiil first, which are both neutral to Skyrim at the time, and could be allies in the next Great War. In order to last, the Stormcloaks should hold off until the Dominion has been bested, which would probably be around twenty years later. Tamriel would be at peace for all of two seconds if the Stormcloaks were to try a conquest, although after the Great War II, doing so would be quite difficult with as few men/women as they'd have.

Overall, Ulfric couldn't become a conquerer. He'd have to take out both his potential partners in Great War II and the largest military power in Tamriel in the span of thirty to fourty years, all while somehow looking good to the people...which is extremely difficult for a warmonger to do.