Hi Ryan,
Im using Drupal 5.7 and Uber RC4 and I was having trouble trying to update one of my countries (Mozambique).
I tried new versions, etc, the change (a small province name change) i did on the file wouldnt show up.
Ended up deleting all orders, removing the country and enabling again. Only then it showed.
I think you should look into this.

Joined: 04/05/2008