» Thu Nov 15, 2012 11:00 pm
Well, consider who your character is, for RP purposes...
A Thieves' Guild player might want a home in a centralized location. Having restored the Thieves' Guild to prominence in Riften, the next step is to establish chapters in the other holds. I'd say Hjaalmarch.
A mage would want to be near Winterhold, and the College, to check in on their colleagues more conveniently. The Pale is closest, I think.
A Dark Brotherhood type would want to be near the Falkreath HQ, so a house in that hold would be best.
Consider that after the Civil War, whoever wins, there will be resentment in the vanquished holds. If you favor the Empire, Falkreath is friendly to it. If you prefer Ulfric, go with the Pale. Hjaalmarch seems neutral.
Also, which hold do you like becoming thane of? You might have to do that, you know.