Classic/Antique Car Repair: 52 plymouth starting issue, piston rings, compression check

Question
i bought a 52 Plymouth 4 door a few years ago, and it starts up fine, but after it warms up for say 20 min. or so, and you shut it off, it will crank and crank and won't fire off. if it sits for 20 min. or so it will then start after it has cooled off some, i thought it was a fuel filter problem, but i checked that already, I was told to clean my points, but is that the points on the distributor?

Answer
It could be a variety of things. The carburetor but be dribbling over internally flooding the engine on shut down. To check this remove the air cleaner. Run the engine till warm and shut it down. With a flash light, not a match, look down into the throat of the carburetor. If there is gasoline dribbling from the jets down into the carburetor, toy have found your problem and you will need to rebuild the carburetor paying attention to the float and the needle valve. If the carburetor is ok, then I would check and probably replace the points in the distributor if the contact surfaces are blue black. Good points the contact surfaces will be a light gray. The coil can cause the same problem. It is supposed to be filled with oil. Remove the large wire from the center of the coil. If there is oil on the wire then the coil is leaking and subject to heat break down. If everything else checks out fine run a compression check on the engine after you have warmed it up. I have seen old engine loose compression by the piston rings when hot. These are but a few things that could cause your problem.
Brad