I believe he had a 6 cylinder and now has an 8 cylinder.
It sounds like the problem is that the starter is drawing so many amps, that there isn't enough left over to provide spark for ignition.
Why not change out the ignition switch to a run/start/accessory one, and lose the push button switch?
I don't like the idea of using a header bolt for a ground. Too much corrosion going on there.

1952 5-window - return to "as built" condition | 1950 3100 with a 235 and a T-5 transmission