falconnm,
If all your statements are accurate, it means your voltage regulator is bad. You said you manually pushed the cutout relay closed and saw the ammeter jump to charge. If this is true then your generator is functioning.
The cutout relay can be adjusted for voltage, but if it doesn't come in at all, my little Echlin book says replace it.
Before I did that I would make sure the fan belt was tight, the FIELD and ARM wires were all clean, tight and in good condition.
If you have a meter, you can pull the field wire from the generator and attach a small good jumper to ground momentarily. If you have a meter on the ARM terminal, you should see the voltage jump as you rev the engine. This will prove your generator.
Although I'm certainly not a automotive electrical guy, it seems like the relay should close as soon as generator exceeds battery voltage. This is usually around 6.5 volts. Your battery is a 6 volt item isn't it?.
Maybe someone else with more knowledge will be along soon.
Stuart