Update! We actually did get around to tackling the mansard roofing. We finished this in September 2013 (and I forgot to update this thread until... now, oops).
Thank you for all of your comments. We wound up extending the uppermost roofline out about 10" to create more of a traditional roof look. This added top gutters (which solved our water flow issues) and soffits. We put in all new windows and had them trimmed out with bright white.
Not sure if we will add shutters on top. I'll try to photoshop it and see how it looks. Next phase is working on the landscaping more.
Here's a before and after!
Q
Roof and siding colors
Q