Generally speaking, you cannot throw more horses at a shallow well pump to get it to draw water. If a 1/2 horse won't do it, more horses won't help.
If I understand, you have a footvalve, then a pitcher pump in series, then a checkvalve, then the shallow well pump. Sounds like there is too much resistance in series.
The footvalve is likely spring loaaded. Why do you have a checkvalve at the pump? It too is probably spring loaded. The valves in the pitcher pump might also be spring loaded. Try removing the last checkvalve and put a bypass valve on the pitcher pump. It should then be able to draw but if the water leaks back to the well, the footvalve needs replacing.