A question that I am not sure how to even ask...

No, the tranny fluid goes in the tranny box filler tube. I filled the oil access on the top of the valve head; its the breather access.

I'm surprised that your car takes 6 quarts as the shop manual and owner's manual stipulates 4+1, but maybe the blocks are different? I don't now, I don't have a '64.

In any case, the oil went into the fill but has not spilled into the il[an, so something is clogging it up.

Thanks for the help...

Most likely: if it takes 6 quarts, the dipstick is too short. (Chrysler dipsticks were notoriously inaccurate.)