Manual data entry is just too unreliable and time-consuming. I don't see how this could work short of integrating OBD-II fuel consumption data combined with some sort of presence tracking.
Regarding automatic tracking tho, the easiest option is Bluetooth based, the app knows the identity of the car, when the phone connects, it knows you're probably starting a trip. And the same goes for connected car APIs, those can much easier take the place of an OBD-II reader.
Then at the end of the month debit each account that used negative gas.
The only thing this misses is encouraging fill-up before empty, but it could give notice when the tank is below ¼ before a trip