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When I first played the game, it was the journey from Helgen to Riverwood. Now, Forgotten Vale blows my mind time after time. And let's not forget to mention the soundtrack! It's near unbeatable! (Insert feels here).
I have played both factions, and I have decided that, for the good of Skyrim, the Imperials work better. If Skyrim broke off from the Empire, not only would the Empire be obliterated, but (eventually) Skyrim as well. That and I don't like Solitude to be in ruins (kind of). So, Imperials for me!