Good thing I'm the curious type and was able to figure this out myself.
As I suspected, the problem was with the pressure switch. There was a pocket of silt hanging out in the diaphragm area of the switch. I assume the silt prevented proper switching operation as the diaphragm was beaten up pretty good. I replaced the switch and the system resumed normal operation. Should be good for a year or two until the silt damages this switch as well, I'll just add that to the pump re-build kit list that I buy to deal with the silt issue.