Consider it this way ...
The car engine shuts down. Immediate heat soak as there is no air circulation or coolant circulation. The fuel (E-10) begins to boil and is released through the vents as a gas. The floats drop and the pressurized fuel in the fuel line expands and enters the fuel bowls.
Most likely the valves in the pump are not opening/closing correctly due to the effects of the ethanol fuel. It is also most likely fouled (as will be the carb) due to zinc oxide and only who knows what is coming out of the tank.
You cannot use a phenolic carb spacer due to hood clearance (BIRD).
Before start, remove the ACL and look into the carb venturies and see if fuel is puddled on the throttle blades (and most likely the intake manifold plenum floor). Move the throttle linkage and see if any fuel is shot (accel pump). No shot, either the bowls are empty or a bad accel pump.
So you crank the engine hoping for a quick prime. You are abusing the starter with extended cranking and there is also no ignition advance retard feature (to allow easier cranking). That pretty ACL acts as a tent retaining the engine heat around the carb and further exasperating the problem(s).
So, the only true way out is with an electric pump, either primer or transfer (tank to mechanical pump) (ideally with return fuel line for cooler fuel) and a clean fuel system with the proper fuel conditioner. The fuel curve has to be adjusted correctly also (larger jets).
Today's' fuel(s) are formulated for EFI and EVAP, not carburetion.
____________________________