Re: I hate roofing too!
Thanks for the lot. I think I see the issue and a way to work round it. You have to place the roof in small sections rather than just the four pieces you have built. This actually gives greater flexibility with the roofing tool.
Your house straight from the gallery. I have changed the connecting bedroom/bathroom wall to a half wall and the roof shows through (ignore the door):
If you create the roof using lots of separate pieces and no overhang into the rooms you can place the half wall easily with no roof inside:
This gives you an idea of the pieces I used, a mixture of half-hipped and half-gabled: