I've done a lot of water well pumps/motors. The motor load on a centrifugal pump is controlled by pump. If the pump is not sized correctly, the motor will be overloaded. If the pump has no head, or discharge pressure, the pump is way off of its curve and the motor will be overloaded.
Typically you are allowed a service factor of 10% for well pump motors. meaning you can run over the rated nameplate amps by 10%, but this will result in additional motor heat and shortened life.
Try taking shut off amps - shut the discharge valve momentarily and see what the amps are, they should drop as you close the valve. don't leave it shut longer than necessary as you will overheat the motor -it needs the water flowing by it to cool it.
Also what type of overloads do you have? Typically need quick trip ambinet compensated.
Has anything changed on the load? more sprinklers, connections etc?
A one time megger reading means little. What you are concerned with is the trend. And I like to meg wells 5 minutes after running.
The best way to meg motors is to do a 10 minute dielectrical absorbition ratio, plot the readings at 30 seconds and then every minute for ten minutes and see what the curve is doing.
Biddle or who ever they are now has some great information on megger
testing.
Anyway check the pump load. Its not always an electrical problem...