The Aldmeri Dominion
What the Stormcloaks don’t seem to take into account enough is the Aldmeri Dominion and its Thalmor masters. The Empire and the Aldmeri were about equal in battle during the Great War, but that was when the Empire was much stronger and more united than it is now.
For the Stormcloaks to beat the Elves, the Empire as a whole would have to work together. Even General Tullius knows this, because he calls the Stormcloaks “fools” for fighting the Empire when they should be fighting the Aldmeri Dominion with them.
Skyrim Can’t Sustain Its Population
As the player explores Skyrim, if they pay close attention to each hold, it becomes clear that not much food is being grown in the province. Skyrim is mostly made up of mountains and snow, so a lot of it is not good for large-scale farming. And because of this, Skyrim has to get a fair amount of its food from other parts of the Empire, mostly Cyrodiil.
If the Stormcloaks win, many parts of Skyrim will almost certainly die of hunger without this trade network, but Ulfric doesn’t seem to know that.
Nord Racism
There is a lot of fascist rhetoric coming from Stormcloaks, and many of Ulfric’s followers say Skyrim is only for Nords. This way of thinking leads to open hostility between the Nords, the Argonians, and the Dark Elves in Windhelm, which is a great example. The last two groups are either stuck in the city’s poorer parts (like the Grey Quarter) or aren’t allowed to live there at all.
The minorities in Skyrim don’t matter much to Ulfric and his Stormcloaks. If they could, they would happily kick them all out. As soon as you play a character who doesn’t share this racism, or as a character who isn’t Nordic at all, joining the Stormcloaks stops being fun.
Ulfric Can’t Be Trusted
Ulfric Stormcloak is known to be a man with big plans. He learned how to master the voice long before he became a rebel. He was well on his way to becoming a greybeard. But it didn’t take him long to stop studying and do the very thing he promised himself he would never do when he screamed the high king of Skyrim to pieces.
There is some disagreement about whether this was a legal challenge or not. Either way, Ulfric looks bad because he knew he would win the fight because he used the Thu’um. His acts were more like those of a usurper than a freedom fighter.
The Reachmen
The Stormcloaks’ main point is that they should be able to run their ancestral homeland without any outside interference. The problem is that this is blatantly false because that is the exact point that the Forsworn of the Reach are making in Spacebar Clicker. The Reachmen, who are a mix of Breton and Nordic blood, were the first people to live in the Reach, but Ulfric strongly disagrees with their right to self-government. He is even said to have violently put down a rebellion in Markarth, which probably started because the Nords were mistreating the Reachmen.
The Issue of Talos Worship
While the Nords strongly believe that Talos is god, many other people in Tamriel think that worshiping him is silly or even hurtful. Because of this big difference in religious beliefs, it makes you wonder why a character who isn’t Nordic would fight for the Stormcloaks.
One example is that Khajiit people don’t need to worship Talos because they have their own set of gods. The Argonians and the different kinds of Elves each have their own group of gods that don’t include Talos.
Thalmor Puppetry
During the main questline, the player can look around the Thalmor Embassy and find a folder with information on some important people in Skyrim, such as Ulfric Stormcloak. The report says that even though he won’t cooperate, he is helpful to the Dominion’s goals. I think this is because his civil war not only keeps the Empire busy with fighting, but it also makes it even more divided. In the long run, it also makes Skyrim easier to attack and take over.
In a very bad light, this new information shows that Ulfric is not only a stupid person, but that the Thalmor are counting on him to be stupid. A quick end to the fighting in the area, ideally in support of the Empire, would be very bad for the Thalmor in the long run.