1951 GMC 100 - Door Glass Replacement 

Good for you showing yourself having a hard time with the glass. It's not easy!! best I can tell my drivers door has the same issue as yours. I think I need to pull the lower hinge. And open the slots so it will adjust farther out. Moving the strike up.

The window crank handle might have a cap screw that has to be removed to access the set screw underneath.

Remove those 2 hex bolts that are hitting the jamb, they are supposed to be counter sunk type heads.