OE,
Sounds like you have a plan. It will be difficult to paint the engine in the car and still come even close to what you could do with it removed. Be that as it may, here are a few suggestions - all of them pretty obvious-:
a. Paint the valve cover with it off the car. Then put it back on when you paint the rest of the engine. Plug the vents.
b. Take the flywheel cover off and paint. Make sure the drip hole is clear.
c. Take out the crankcase breather. Plug the hole. It should be black.
d. Take off the starter and generator. Both should be black.
e. Take out the distributor, Plug the hole. Again black.
f. Take off the fan. Black.
g. Take off the carburetor and fuel pump. Black and natural, respectively.
h. Air cleaner. Off. Black.
i. Remove fan belt. Natural.
j. Remove all hoses. The center lower metal elbow - black.
K. Try to isolate the rest of the engine from the inner fenders and fire wall. I would take out the radiator. Easy and will give you better access to the front of the engine. When you try to get paint to the rear of the engine protect the firewall with a sheet of paper or thin cardboard.
Others probably will point out the things I missed. I admit that I have never tried to paint an engine while it was in the car.
I wish you good luck with it. Use the correct color (Industrial gray) or what Filling Station and Cof40s sells in a spray can. A paint brush will add to the difficulty.
Charlie