Going all the way back to TES I: Arena, there has been a continuous timeline being built. But I'm wondering if Bethesda has painted itself into a corner. They designed Skyrim in such a way that it allows the player to decide which faction would win the civil war: Stormcloaks or Imperials? That decision is incredibly crucial to the continuing Tamriel timeline. If the Empire wins, the consequences really won't be all that drastic, but if the Stormcloaks win... [More discussion on a Stormcloak victory in this thread, starting with post #55: http://www.gamesas.com/topic/1513947-justification-for-joining-stormcloaks-as-non-nord/page-2] At a minimum, with Skyrim separated, the Empire is no longer contiguous, with Highrock hanging off by itself. Would it opt to also go it alone? What happens with the race relations inside Skyrim once the most xenophobic element of Nord society in charge? (Sort of like Afghanistan after the Taliban took over.) Would the Empire seem so weakened that the Aldmeri Dominion thinks it's time for Great War, Round 2? Would Morrowind consider coming to the "rescue" of the Dunmer that had fled to Skyrim after Red Mountain blew -- and then be treated poorly by the Nords there? Would Black Marsh join in such a venture, given that Argonians in Skyrim are treated just as badly (if not worse)?
So many possibilities, and design-wise almost irreconcilable, given the two distinctly different paths.