SJE MicroMaster Plus Pump Switch Not Working

I recently moved into a house that has a well installed (appears to be only 6-8 feet deep) in the crawl space for lawn watering purposes. The well system consists of an air compressor as well. The SJE pump and the air compressor plug into each other (pump has both male and female connections), and then you are to plug the connected pair into a power source (regular outlet or extension cord). Initially, I did this and the pump seemed to be working fine and the air compressor was doing its job. So, I unplugged them from the power source. I thought "Great, this thing works!"
However, I plugged in the thing about two weeks later, and nothing. It appears that the well plug is the culprit. When I plug in the air compressor directly, it works, but when combined with the pump, nothing happens.
Does this mean I need to replace the well pump? If not, any suggestions as to what I can check/do to get this thing working again?
The water sitting at the bottom of the well appears to be minimal and the actual pump is sitting underneath the water. In the case of my 6-8 feet well, about roughly how much water should always be in the well?
As you can tell, I know virtually nothing about wells and well pumps. Any help you can provide would be greatly appreciated.

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