1. Add lock code to your phone
2. Open the app without a debugger attached and start monitoring for significant location changes
3. Minimize app
4. Turn off iPhone
5. Turn iPhone back on.
Now if you wait 3-5 minutes in the same spot, your app will be woken up and will get a significant location change. Much simpler than driving and easily reproducible in the office.
Now to know when the app actually wakes up while you're in the lock screen, I added a local notification as part of the startup process. Now we just keep the phone locked for a few minutes until it shows the local notification, then you unlock it and see the logout problem.
Hope that helps everyone else!