As a stranger in a strange land, sometimes you need to get a different perspective to see how you might fit in. Jeremy gets his chance to see Equestria from the bottom up when he gets in trouble with the law. Ponies have such a happy, peaceful society that it's easy to forget that perfection doesn't exist, and there's always going to be misfits and the disenfranchised.

“It is said that no one truly knows a nation until one has been inside its jails. A nation should not be judged by how it treats its highest citizens, but its lowest ones.”
― Nelson Mandela