It is common for those old systems to not charge at low idle but as you know it should pick up when you throtte it up. As the generator heats up it gets less efficient and as the coils in the regulator heat up they get less efficient also. Old connections corrode and build resistance I would guess that a combination of those factors is what is causing your problem which is the generator doesn't have enough umph when it is hot to pull the cutout relay closed. If it were mine I would remove the cover from the regulator and lessen the spring tension on the cutout points just a smidgen. The cut out relay is the one directly connected to the BATT terminal. The cutout points will be open when the engine is stopped. Another way to identify the correct set of points is to loosen the generator belt and remove the belt from the pulley. Then push the points closed with your finger. The cutout will cause the generator to motor, the wrong ones will not. Do not adjust the air gap,adjust the spring pressure, on some regulators it is a screw, others you have to bend the tab that holds the dead end of the spring. As an aside emery cloth should not be used on points, always use sandpaper.
Agree with you on the new regulators mostly junk. When ever I need a 6V regulator I go to Ebay and buy an old stock unit.
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