Fall sounds like a good time, since it's cold, but not too cold. 

I like an apartment building. Mainly cause I live in one, but it's also practical: less buildings, thin walls, so any disasters (like a burglar or weather damage) can be heard by the neighbors, and they tend to be two to three stories, so flooding won't be too much of an issue. Also, my apartment building has fireplaces, and it's relatively cheap for apartments. The one big problem is fires, though. You're pretty much screwed when a fire spreads. 

Super Walmart, Target, similar areas, I'm game for that.