No bear with me, because this would NOT be for Skyrim, but COULD be started in Skyrim... If started in Skyrim, you'd have Skyrim II with the Civil War obviously still being an issue, as well as the Thalmor... IOW, you'd only jump ahead 18 years or so. You'd be son or daughter of the DB, the High Queen's (Elisif, since Ulfric may have died) new right-hand man/woman instead of the traditional TES "prisoner"... You could even have the option of "recruiting" your parents for early help. If not a Skyrim based game, then, all bets are off. With TES's wonderful open-ended designs, a new game could be split into 9 MQs across 3 generations, depending on the actions of the last generation. As long as they're open, it would work. For example... say it starts right after SK... you start by either expelling the Thalmor, joining them and strategically retreating in favor of a more covert war, or you ignore the MQ completely and settle down, the Thalmor are out of SK, but you won't know why. Then expand from there, similarly, with 3 possible MQ conclusions to create 3 new MQs for the next generation. Such cool things that could be added are convos between mama and papa that begin kiddo's journey like, "You know, I hear that Helgen is bustling after being rebuilt. That juniper berry mead is very popular with the Imperials..." Then as the child, you'd go out and visit those world changes, some old shopkeepers (aged, since dynamic aging would have to be in there anyway), some new, new houses or additions built on, or whole houses or even towns, changed by men or disaster.
Don't know about you, but playing a 60-90 years span seems really cool to me. "Wasn't your mother the DB?" "So, how does it feel to be the son of the Harbinger." Just some one-liners to throw in.