Does the Location Service need a data connection to work effectively?

Depends on the method you use. If you are using "fused" mode, location service will use a combination of wifi/data/GPS - whichever gives the best result

I have had good results using the HTML5 Geolocation api through the webviewer as opposed to using the native Location Sensor....

Depending on your device, airplane mode may or may not turn off GPS.

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