The story says that his mother took his cell phone and his father is active duty deployed in the Middle East. But I, too, wonder how it was that he thought some random neighbor could tell him where his school was if he himself didn’t know it... and by April, if he’s been going there since August, he should know where the school is. If it’s so far away that he has to ride a bus, I doubt it’s walkable. I, too, think he was Trayvoning around the neighborhood looking for empty houses.
If his father is active duty, then he is likely to have moved recently. He is also likely used to living in an environment where the relationship between neighbors is more casual, secure, and people with guns are actually secure and confident.