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Okay...yet another one I am going to probably get some hate for, but to hell with it. When I go through the Civil War questioned, on the off-chance I do because I think it's a bit boring, I side with the Empire. I tried one time to side with the Stormcloaks but remembered why I don't and betrayed Ulfric during the jagged crown quest. I understand that neither side is truly the best choice, but I do believe the Empire is, on the whole, a better option. This one's going to be a bit longer just on my rant about this.
Let's start with main problem...Ulfric Stormcloak. The leader of the rebellion and "the true high king"...let's start with that. Nordic tradition states that a jail is allowed to challenge the high king in fair and honorable combat for the crown. This tells me that, as long as your opponent can use something like magic or the Voice, it's valid to use. There is more evidence to suggest that Torryg, who had ruled as high king for quite a long time, did not learn the Voice from the Greybeards as he spent more time focusing on his duties as jarl and high king. Ulfric's crime is that he murdered Torryg which is more focused on that he Shoutedat him to win the fight, something would be punished by Nordic tradition.
Let's look at Nordic tradition and Ulfric beyond the high king. He claims to care about Nordic traditions while flouting them. The Greybeards are bound by ancient rules, unlike the Dargonborn, to only use the Voice to train future Grebeards and the Dragonborn, and to seek enlightenment through their training and meditation. Even if Torryg could Shout, by the Greybeard's training, they would not be allowed to use it for personal reasons like combat. Ufric broke this very sacred Nordic tradition and basically ignored the teachings of the Greybeards who are reveared by Nords.
Continuing this thread, let's look into Talos...God of Humanity. Talos may have been a Nord, but he is not a Nordic God and was basically brought to the Nords through inquisition by the Empire. The Nordic Pantheon has fallen by the wayside in Skyrim in favor of the Divines save for a few pockets here and there. Ulfric focuses so much on Talos that he not only seems to ignore the other Divines, equally worthy of worship, but also ignores the gods of his ancestors such as Kyne, Shor and Tsun.
The Stormcloak Rebellion...strange that it's named after the man who leads it rather than something related to the traditions they claim to be defending. If Ulfric truly cared, he wouldn't have named it after himself and made himself the figure head. How many Stormcloaks say they follow Ulfric but don't really mention that they're fighting for the Nord way of life. It just doesn't sit right with me that the rebellion and his soldiers seem more focused on him rather than their actual cause.
Okay, so that's all I'm going to say on Ulfric because I decided to do this on the Civil War and not Ulfric. Now...why don't we look at the aftermaths of picking a side in the Civil War questline and even the peace council? Let's start with the Empire. The main jarl that people hate for the Empire is Maven Blackbriar who is a businesswoman who deals in underhanded deals with the Thief's Guild to stomp out her competition. Would she be who I put in charge...probably not, however, there's a point to be made. After becoming jarl, does she have a reason to continue to use the Thief's Guild services? She honestly didn't need them in the first place, most likely and simply uses them because they'll mess with her competitors for her. However, even without being jarl, she doesn't really have a need for the Thief's Guild and, outside of what they do for her, runs a successful and legitimate business making mead.
Now, Maven's Stormcloak equivalent is Thongvor Silver-blood who rules over Markarth. As you know, the Silver-bloods control the silver mines around the area and employee slave labor of both the Forsworn who are captured and even prisoners, political and not. You yourself can be thrown into Cidna Mine simply for trying to uncover the issue with the Forsworn directly in the city and disturbing the peace. Maven is a shady businesswoman, but there is no evidence that she actually employs slaves to do the work that makes her business run, even for the simple jobs that anyone can do.
Now, the aftermath of the Empire victory, really just leads to people being butthurt that Ulfric lost. Yes, the priest of Talos in Whiterun is found in prison if you side with the Empire, but there is no malice in the action as the Thalmor most likely would have killed him where he stood if they were there. Ulfric's supporters complain about how they would continue to fight for him, but it seems more like children who are complaining that they should've won because they were in the right...kind of like a "It's my house, so I should win" kind of feeling to me. Most other npcs, neutral or empire supporting, seem to be happy or at least neutral with the arrangement and life goes on.
If the Stormcloaks win, from having watched a video on these outcomes since I can't bring myself to do it, it actually harms the people. Adrianne Avenicci will tell you, if you sack Whiterun for the Stormcloaks, that she does less business and the only reason she has any left is because her husband is a Nord. It would seem that Stormcloak prejudice extends even beyond elves and argonians. The innkeeper of the Bannered Mare complains that the Stormcloak soldiers routinely get drunk and mess up her tavern and leave, leaving the workers to clean up the destruction only for it to happen again. This reminds me less of soldiers who are fighting for the people and more mercenaries who are in it for the glory and the spoils.
I just can't find a good enough reason to support the Stormcloaks, but for those of you who make that point that the Empire sides with the Thalmor, it's not by choice. The Empire and Aldmeri Dominion have a very uneasy peace due to the destruction of the Great War which the Dominion mostly won. The Empire is looking to increase their strength to take on the Dominion, but they are trying to do so in secret. With Talos worship being banned as part of the treaty, the Empire only banned the public worship, but wasn't really too fussed about enforcing it as Lokir in the opening cutscene hints at. Ulfric stirred up trouble about Talos and the Thalmor stepped in, forcing the Empire to crack down on something they didn't really care too much about.
For a final thing, this isn't really a fact thing, but let's look at the future. The Empire lost the Great War, the full might of it, and the only province that could stand against the Dominion was Hammerfell who is now no longer a part of the Empire as part of the White Gold Concordat. The Stormcloaks win the Civil War because you as the Dragonborn intervene on their behalf, but you are no immortal from an in-game standards. I am not confident that the Stormcloaks could make a successful attempt at taking on the Aldmeri Dominion, much less hold Skyrim from them should the Dominion were to take advantage to get around the Empire and start taking Tamriel. Again, the war is only won based on who the player decides to side with.
I just can't side with the Stormcloaks as they're using the excuse of freedom to basically demand control of the province so that they can enforce their own rule upon the masses. The Empire, while currently weak, is at least trying to keep the people of the Empire safe by appeasing the Dominion just enough to avoid the looming second Great War from coming before the Empire is ready to fight back and have a chance of winning. Long live the Empire...and hail Sithis.
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