Using an analog voltmeter (has needle that swings as opposed to a digital meter), connect the positive lead of the meter to ground which is the plus side of the battery and the negative lead to the BAT terminal on the regulator. Start motor and rev to say 1500 rpm and briefly touch the disconnected field wire on the regulator to the ARM terminal on the regulator - voltmeter should move up to 7.5 volts or more, but do not perform this test for more than say 5 secs. Repeat this test by connecting the negative lead of the voltmeter to the ARM terminal on the regulator. If no result remove generator for testing and repair and if you get 7.5 volts or more, replace the regulator. Your charging voltage should be 7.2 to 7.4 volts. The reason for using a analog voltmeter is that the ignition system will make the readings on a digital voltmeter erratic!!! Report back.
Your choice of the Stromberg carb is good in my opinion, but does your E fire distributor have mechanical advance and perhaps vacuum advance also? Curious.