My guess is that each cottage has a pressure tank with its own pressure switch, and then there is a 12-2 UF that runs from the pressure switch to an in ground splice box next to the well. All the cottages are fed from the same transformer, so as long as the legs are matched up properly, it wouldn't matter which cottage was calling, as they all can trigger the pump, and send power to the pump from more than 1 pressure switch at a time. Electrically the pump wouldn't know the difference. Safety wise less so, but electrically it would work just fine.