User blog comment:Spritydove/Deeper Thought into the Civil War/@comment-152.133.14.7-20120709134516

The only problem with combining holds is that each one has a significant amount of history and tradition behind each Jarl's authority. There may not be much to Winterhold now, for instance, but it used to be one of the most politically significant regions of Skyrim - I agree with the Northern Douche that it should be rebuilt after the dust settles. Falkreath is almost as ancient, and its people would almost certainly balk at being "assimilated" under Whiterun or Markarth's leadership. This is a cultural concern, not a pragmatic one, but in the long run I think the political success of a free Skyrim has alot more to do with culture than logistics.

Also, getting rid of the Jarls altogether (as suggested by the Imperialist sympathizer below) is the fastest surefire way to undermine your authority in Skyrim - if the Empire wins in Canon, it'll be because they garnered the Jarls' support against Ulfric by allowing them to retain some level of autonomy. Take away that concession, and the people of Skyrim will quickly realize that the Stormcloaks were right about losing their country and their identity under the Thalmor-powered Empire. Centralizing exerted authority over an occupied or "forcibly reunified" nation has been shown throughout history (Tamriel's as well as IRL) as the worst possible method of colonization - or, in fact, to impose a different regime or administration on a large demographic who don't want it. Centralized government is a lazy and negligent form of leadership, ESPECIALLY for a place as large and varied as Skyrim, and every instance of true oligarchy in Earth's history has proven to be quite short-lived in comparison to other types of government.