Insert printing drama

I've always considered myself ok with computers, about a 6 out of ten on the competency scale I guess. But for the life of me, I just can't get inserts for my personal filofax printed out properly!

I've tried printing one side, then flipping and printing the other. I've tried to graphically represent what generally happens...

Whereas what I want to happen is this...

I've tried flipping the paper differently, setting the pages up differently, even playing with the templates and move the second page over to the left more and it still prints out wonky. I'm running out of paper to play with now! Help!