The biggest "secret" is to make ALL door adjustments before the weather strip is put on, including the latch and striker fitment.
All is not lost.
Did you rebuild the door hinges? If not, I would do that before proceeding any further.

The striker will often give you false readings as you make adjustments of the door. As the door is closed, the striker will push the door out of position without you realizing it. Remove the striker from the truck
Without the striker in the way, you will have more freedom to move the door wherever you need to. If the cowl is peeling off the weatherstrip, you can slot the hinge bolt holes at the hinge pillar to allow the leading edge of the door to extend out from the cowl. The Factory Repair Manual specifies "flush to 1/16" out from cowl to avoid contact with weatherstrip when opening door.
Another option to stop the weather strip from getting torn off by moving the door to the rear a little, if you have room at the rear door gap.
Once you solve the weatherstrip issue, and the door fits the door opening nicely, you will need to do what you must to make the latch and striker work to keep the door closed tight.
Is the striker a new reproduction? They can be problematic, but we can cross that bridge when we get to it.
I cannot stress enough how important it is remove the striker before attempting to adjust the door to the opening. (In case I didn't convince you already,)
Carl

Last edited by 52Carl; 07/14/2019 8:57 PM.

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