Dusky Hollow looked the most interesting to me. It was the only Clakker settlement that still had a Southbounder operating. The other towns' had shut down. Of course, the real reason it's my favourite is that there's no option to vote for it.
NDW, New Yolk City is smaller in the game than it was in the past due to Outlaws taking their resources and making it an unpleasant place to live, encouraging Clakkerz such as Farmer Beeks to move to the country.