I'll try to answer the questions in order.
The best place to get oil pressure from is the OE oil pressure sensor port.
The sensor on the rear of the cylinder head is not the sensor you seek. There is no oil pressure in the cylinder head.
The sensor near the starter is the oil pressure switch. It is wired to the electric choke so that a key-on, engine-off event doesn't cause the choke to open with the engine still cold. I think the best bet would be to find a T adapter to leave the OE switch in place, but still be able to plumb in a second sensor.
The manifold heater is also driven off the oil pressure switch, again so it is not continuously running with key-on, engine-off. If you want to know if it's working, just start the engine and try to feel that round thing on the bottom of the intake under the carb. It should begin to feel warm after about 3 minutes, long before the metal of the intake gets warm. Easier to tell when it's cold out.