Lets back up a few steps before we proceed further.
Did you rebuild the hinges? If not, there is a good chance that worn hinge pins are causing door sag which cannot be compensated for at the hinge pillar.
Worn hinge pins are the #1 cause of beat up door latches and poorly fitted doors.
Carl

1952 5-window - return to "as built" condition | 1950 3100 with a 235 and a T-5 transmission