As for my character, he ended up filthy rich and high up within the legion. I could see him usurping Tulluis for control of the Skyrim legion. With it under his firm control, and it filled with legionnaires unhappy with the state of the empire, he would have marched south for the Imperial province. With the legion as the main fighting body, it would be reinforced by my characters personal army of huscarls and supported by the reforming blades (aiming for revenge and to retake their position within Tamerial society). With so much gold amassed, a sizeable contingent of mercenaries could have also been recruited and any of the flocking plebs, coming to the Dragonborn's banner, could be armed. Not to mention being Thane of all of Skyrim's holds, and having done extensive favors around all of them, am sure some would send some men to help.
The Empire would be, assuming all quests of the game had been completed, looking for a strong leader. I don't think anyone would oppose (that much) the rise of a new Dragonborn Emperor.