Kimarous said:
I sided with the Imperials. Not so much for any particular love or loyalty to the Empire; hell, before I got the game, I was all "the Empire deserves to collapse until a new leader can reunite Tamriel." I changed my tune when I actually met the Stormcloak leaders... they're TERRIBLE! Dawnstar has a paranoid wreck, Riften is oblivious that she has no real power, Winterhold just mopes and whines instead of actually trying to fix things, and Ulfric is so caught up in a war he caused that he neglects the citizens under his direct control! Hey, future High King; I think you can step away from the war room for a few minutes to take care of the serial murderer on the loose! At least the Imperial leaders seem halfway competent (well, minus Falkreath, but his steward keeps things in order).
You will find the leaders are often semi-parallels of each other.
Winterhold: Morthal. Both aren't liked by their people. Winterhold has legitimate reason to be unhappy - his entire town fell into the Ocean. Well, a tiny bit survived, but W/E. Fact of the matter is, no-one listens to him. He sends the Dovahkiin on quests to regain some status for Winterhold - collecting artefacts of her past to gain some standing with the other Jarls - but he is almost literally a Jarl without a hold. His biggest failing is that he hates the Mage college, but that is because he suspects them (Incorrectly) of causing the great collapse. Morthal is in the opposite problem, where she trusts the mage, but the town don't and don't like her decision making.
Dawnstar: Falkreath. Both more obsessed in their personal endeavours than in the town they govern. Dawnstar is in it for the Glory of the war, to drive the Imperials out and reclaim Skyrim for the Nords. Falkreath is in it for his own personal pleasure. He couldn't care less about his hold, so long as his belly stays full and bandits fill his coffers.
Markarth: Riften. Both aren't run by the Jarls, but by a corrupt family using another faction to elicit control of the hold. In Riften, its the Blackbriars and the Thieves Guild. In Markarth, its the Silverbloods and the Forsworn. Hell, these are probably the two most paralleled towns. They are at the farthest point on the map to opposite directions of each other, both have the same problems, both have the same sort of leader and both are two of the largest cities in the game (Not sure exactly where Solitude or Windhelm sit in size comparison to Riften).
And Finally, Solitude: Windhelm. Both are under a rather lackluster leadership ATM. Ulfric is obsessed with the war, Elisif is just plain incompetent in command. Both suffer from problems: There is a murderer in Windhelm, a Necromancer witch queen in Solitude. Both are the capitals, and in both the Stewards run the hold whilst the other does whatever (Elisif mope about her dead husband, Ulfric go on about the war).
Now, I chose Stormcloaks. My reasons for this can be found on any number of other threads; use the search bar.