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I'm thinking either Honeyside or Vlindrel Hall. I like Markarth but it is inhabited by Stormcloaks at the moment. When the Imperials drive them out, do Imperial Soldiers move in or do the regular Markarth Guards return?

Get Vlindrell Hall, Its much cooler because of the stonework.

Imperial soldiers come in. If you have to choose between honeyside and vlindral hall I would say vlindral hall is better but in my opinion the best house is hjerim if you can get it unbugged

Everyone in Windhelm will hate me after I kill Ulfric, so that's kind of out of the question. I wish the faceless, ex-adventurer, sweetroll-concerned guards would come out of hiding. And does Jarl Igmund return if the Imperial get Markarth again?

You should buy the one you like the most.

You should buy all of them.

I can't decide between Markarth or Riften city-wise. Markarth seems like a heavily fortified castle/city in the middle of a hostile place, which is awesome. Riften, onthe flip side, is in a pine forest with a Fishery behind it, and Honeyside has a Garden! Also, is there any point at which the generic guards come back for either city after the war?

I like the house in Markarth the most. I also like the city of Markarth the most. It's just a unique area.

^Same here, Markath is my favorite city and Riften is corrupted and filled with beggars and dont forget about the Ratway.
But i gotta admit Markath is pretty corrupted to since the Silver-Blood family runs the Cidhna mine.

The Silver-Bloods get kicked out after the war, I think.

This might sound crazy, but Breezehome (in Whiterun) turned out to be all the house I needed. I'm not so into the displaying of stuff, but I wanted at least two chests, and I like that it's next door to a blacksmith. Plus, Whiterun is in a very central spot on the map.

The only negative for me is no arcane enchanter, but I can fast travel to Dragonreach for that, and I usually enchant in bulk, so it's worked out.