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I'm always left curious as to why so many assert these factions are in any way opposed to one another. There is no reason, unless you choose to make one up for yourself, as to why you can't be in both or honestly in all factions with three exceptions. You can't side with both the Imperials and Stormcloaks and you can't side with the vampires and the Dawnguard on the same playthroughs. The other exception pops up in Dragonborn where the choice is some Nords or some reiklings.
My dear mortal, don't you realize? The secret to my winning this board is the fact that you can grow without limits while the others never surpass theirs.