So, I've been playing a Crusader Kings 2 mod known as Elder Kings, which takes place during the 2nd Era of The Elder Scrolls Mundus.
I began as this simple guy:
The Thane of Ravenscar in Northern Skyrim. He was a brilliant soldier, but fate would have it that he would die young after a duel went wrong and killed both participants.
His Daughter, Fralia, would have a bit more success, but died at age 59, leaving behind three living children (her eldest son would die from an angry mob). Her son Knud would then reign for not longer than 6 years before dying to a Magicka disease. His only son Stern died at age 18, leaving the Thanedom to his eldest sister Sissel.
Sissel's reign was long and just (thus the nickname), and she expanded the reaches of her Thanedom in the decades to come. When she died, having no legal heirs, the Moot decided that her niece through her deceased brother Stern would inherit the throne. Merillis had acquired several key lands through inheritance and conquest, and with it, brought the Thanedom of Ravenscar into her larger realm of the Jarldom of Haafingar and Hjaalmarch. Alas, she would die the same year as Sissel, from the dreaded Knahaten Flu, which destroyed a majority of Tamriel's population.
In Merillis's place came Jarl Samar "The Lady of Haafingar". She would acquire even more lands through conquests, and she would acquire a marriage to Prince Delvoni (who is still alive in this campaign, currently 257 years old) of the Great House of Hlaalu. Her son would become the most important member of the dynasty, by forging his own destiny. Samar would die in battle at age 20, leaving the door open for her son Stern to inherit the Jarldom at 10 years of age.
When stern came of age, he would break away from the Kingdom of Haafingar, and create the Kingdom of Hjaalmarch in it's place, with his base of operations in Solitude. He would later conquer Whiterun and grant the Jarldom to his grandson (the current King Stern "The Pure"). Stern lived for an extremely ripe old age of 84, with ten children, each granted their own lands within Hjaalmarch, and an evergrowing dynasty awaiting.
The major players in Skyrim at the moment are Hjaalmarch, The Kingdom of The Rift, The Kingdom of Winterhold, The Morrowind Great House Redoran (invading from the East), and the encroaching High Rock Kingdom of Camlorn (from the West). Skyrim's fate rests between the Bretons, the Dunmer, the Nords, and the Reachmen.