When I first got the convertible with a stock (non0numbers matching) 440, it would run fine with no over heating is I drove under 50 MPH, when i tried to drive faster the engine would overheat, and once it overheated, it would not run cool again unless I let it cool down for a day. I tried the usual stuff and no change. The engine had the original steel shim head gaskets and at a point they must have been letting some cylinder pressure into the cooling system which air-locked the system preventing the water from flowing correctly.
Since I built the 505" stroker for the car using a correct date code block, I just replaced the old engine, and the new engine didn't have the overheating problem.
The engine removed was sold, so I never could confirm for sure if new head gaskets would have fixed it, but I an pretty sure that was the problem on that engine.
As you mentioned, it drove ne crazy, tried different radiators, fans, shroud/no shroud, thermostats, hoses, water pumps and such with nothing making a difference.