Sounds like a great car you have there. Welcome to carburetor land. This used to be common knowledge, but now it is a history lesson.
Never pump the pedal on a hot engine as that floods it. That divorced choke is sitting right on the exhaust crossover on the intake manifold. It will stay HOT for a long time. Thus, the choke will stay wide open. The beauty of that type choke is that the bi-metal coil inside the housing adjusts itself to the temperature of the manifold. So a cold manifold will close the choke, a hot manifold will hold it open.
First start-up on a cold engine, you pump the gas pedal once. A freezing cold day may require several pumps. That squirts some gas into the carb, closes the choke, and sets the fast idle speed. The engine should start and run at around 1500rpm to warm up fast. Once the engine heats up, the choke will open, the idle speed will slow down after you tap the gas pedal to release the fast idle cam. Finally the engine will be at operating temps, at curb idle speed, and the choke will be totally open.
After driving around, if you stop and then re-start quickly, it should start right up without touching the gas pedal. If you wait a while, and the engine cools, it may or may not start right up. This is a judgement call on your part and experience will come into play. Try to start it, and if it doesn't, tap the gas pedal once for some extra fuel. Do NOT sit there pumping the gas as you will flood it for sure.
This is why the factory changed from the manifold mounted choke stove, to the hot air choke, and finally to the electric choke. Emissions and starting ease improved as a result. It is too bad an 1980's type electric choke can't be easily back-fitted to that 1960's old style carb. I tried but failed. I think the electric choke is the best kind.