If you're planning on a dark gray shingle (you may want to look at an Owens-Corning shingle called Driftwood which is a gray/taupe shingle) then I would paint the half timbered area a color that coordinates with the shingles, going darker on the wood portions. A new front door and some landscaping would be the first things I would do. I would also paint all the trim and the garage doors the darker color used on the wood framing the stucco.