I have built a bunch of single family homes like this...built, not designed.
I never liked building the dormer on top of the rafters. 9 times out of 10, there is a knee wall inside anyway, so building them on top was really of no benefit as far as space goes.
I'm with Hokie on his original post, I wouldn't even consider brick here. The last few houses I built like that, I convinced the owner to use Dryvit, lick'em stick'em stones or a high-end siding. There is just too much movement up there.