Elevation Transitions

The house was built in 1977 as a traditional brick ranch. In 1992-ish, the 3 car garage and upstairs was added. Our request to the architect was to make it more more coherent, and give it more of an Arts and Crafts style. Here's the drawings for the as-is elevation, an overlay of the two, and the first draft of the to-be elevation:

We've talked with four contractors about the plans. Today the house is crawling with people figuring out what's what. I guess it's progress, but it still feels like it's a long way from moving in.