A list would help: what materials cover the side? does roof fully cover? How many skylights? Does side entry shield indoors from hot sun, and from cold and wind?

Are any materials in disrepair? if they are, what's the direction at this time?

just to see -

Which part of the house are you trying to match? The flat-roofed addition, or the gable core? I can't see how you could bridge those two very distinct styles.

The flat-roofed addition. It’s what you see from the street. We’ve kind of mixed styles a bit. It may not work for some but people in the neighborhood have been really positive about the change.

Can you post a pic from the street and the approach to the front door?