I don't really think about who lives there whenever I have made a map of a large piece of land. I just try to make it look as good as I can. It doesn't even matter if the names are random. I find that if I manage to make a map that I like to look at then I can think up who lives there later. If I don't like the way it looks I will throw it away and it won't matter who lives there.

Now dungeon maps is the exact opposite. I think of who lives there and design the dungeon around that. The high wizard of Kalor is going to live some place completely different than the warlord of Xar. I let the environment shape the people in a world map and the people shape the map in a building map.