Board Thread:General Discussion/@comment-2600:1700:FA70:24C0:90A5:712:EC1:E377-20181221144647/@comment-26213507-20181221150602

I would probably avoid choosing a side at all; that way, the war continues, allowing for easy pick-ins after every battle, theoretically. In addition, the unstable atmosphere of war allows for easier travel than if a side is chosen.

Of course, if you truly want to pick a side, I would choose the Stormcloaks. Since they would separate from the Empire, securing Skyrim would be much harder with only the remnants of the Stormcloak militia, so Skyrim would be much more unstable if you chose them than the Imperials.