Addition:
I implemented a one time location update via CLLocationUpdate for testing purposes when the user resumes my App from background to force the system to calculate a high accuracy location.
This "workaround" indeed helped to accelerate triggering other apps which are monitoring similar geofences, but not my specific CLMonitor instance, which remains stuck.
As I mentioned already, killing and relaunching the app helps to trigger an entry event. The events date is the time of relaunching the app and not the entry time.
I am making a few REST calls inside the monitors event loop, which should only require less than one second under good conditions.
Also the testing geofence is located in an area with a lot of Wifi APs. Other Geofencing Apps which may use the old API are just working as expected.