When you said " I then put a bit of oil on it, and rotated it inside the die without the decapping assembly." did you remove the whole center stem with expander ball or just the decapping pin off the bottom. Also when you rotated the case, was the case all the way in the die or was it sticking out about 1/2". Try using the die with the whole threaded rod removed from the inside the die. If you can't push in a lubricated case all the way in till the shell holder hits the bottom of the die an then withdraw the case, you probably have a problem with the die.
From the picture of the case mouth it looks like you only had the case in the die far enough that the case mouth was just entering the die neck-shoulder junction.
From the picture of the case mouth it looks like you only had the case in the die far enough that the case mouth was just entering the die neck-shoulder junction.