Here's part of the Hollywood schematic which is probably similar to yours.
Williams flipper swtich voltage (resized).jpg
If you measure from the 30/yellow wire lug on the transformer to the 80/black wire on the transformer you'll measure about 50 volts AC. If you move the meter probe from the black wire on the transformer to the black wire on the flipper coil lug (or any other coil lug) you'll still get 50 volts. If you move it again to the 86/black-brown wire on the flipper button switch in this schematic you'll still measure 50 volts between that and the 30/yellow wire. All that really tells you is that the wires and flipper coil are good. It doesn't tell you anything about the flipper button switch.
If the Game Over relay switch in the schematic is open and you measure the voltage across the flipper button switch you won't see 50 volts because even though there is a path back to the transformer through the flipper coil, there is no path in the other direction to the 30/yellow wire on the transformer that would complete the circuit.
I suspect if you were to jumper around the Game Over relay switch (and any other switches between the 30/yellow wire and the flipper button switch) that the flipper would start working.