What's with the Riften hate? You need the seedy underbelly in real society so the rest of you can feel righteous and you get to keep your hands clean. You need us.

I don't have a hate on for any particular city, but I did chop Nasim's head off.
"I get to the cloud district all the time mofo!"

Alot of Markarth hatin'. As Epikal said, come prepared.

Well I would never kill an entire city, because all cities have at least one NPC I'm sympathetic to. If I had to choose, I'd go between Windhelm and Winterhold most likely (though Dawnstar is also ripe for some population control )

You obviously haven't actually tried this because the amount of "essential" NPCs in any city is staggering and makes a "Cleansing" no fun really.

I have nothing in particular against the major holds. I usually head to Solitude or Whiterun if I'm in the mood for guard-killing, though. The moat around Dragonsreach is getting pretty crowded. On my first play through, I was a Bosmer archer and accidentally killed a chicken in Riverwood. Faendal immediately wanted to test my skills. About an hour and several levels later, there were two children and a certain essential tavern keeper left.

Despite my allegiance with the Thieves Guild, I'd love to introduce the Black-Briars to the business end of my dagger. I like Riften because it's seedy (although the amateurish thieves running around stealing goblets irritate me). When I first hit Markarth, I loved how unique it looked, but the layout of the place gives me a headache, along with above-mentioned bugs.

Markarth or windhelm

Cheers

This thread gave me a nice idea:

I'm gonna mod myself a small city somwhere near Hammerfell and fill it with hundreds of Nazeems so I can burn them to Oblivion with my fire storm spell

Hmmm.... I've ran guard massacres in just about every hold by this point. I've not killed everyone in a town yet, but.... hmmm, that's got me thinking.

Now, of course, should I ever attempt such a thing, it won't be in Riften. My current character has too many friends in Riften, and as a rule of thumb, he doesn't misbehave in his own back yard.