"I guess wandering's in my blood." Or rather Zenigata's. On occasion Oscar does wonder what it would be like if he stayed in one place for more than a couple weeks. But he dismisses it. The home of his birth is probably a burned wreck, and he thinks that no place would accept a person like... him. So flawed, so defective as a wastelander. When he and Zenigata split, Oscar may have sobbed the entire way to the next town.

He cut out the one person that accepted him, even if sometimes he doesn't understand him. All because he lost control...

In response to Joshua's question... "You want me to be honest? It's crowded, and it makes me nervous. I never really liked cities. Plus New Vegas is filled with things I don't understand and sometimes I don't want to."