awm03 - That design is really amazing, thank you! capist - Thank you for your mock ups as well. I am a very visual person, so seeing these examples really helps. And the more I think about it, the more I agree that incorporating a subtle Craftsman vibe is probably the right approach. I have always loved the farmhouse look, but I'm realizing that it just doesn't work with our house. And because our house already has such wide room pitches, it already has a slight Craftsman feel. I am surprised to see that I like a darker color better and I think a more earthy tone is better because it works better with the red brick. I am really liking some of these brown tones. A new, wooden door is already on our short list and I love this example. I am a big fan of double doors, so we plan to go that direction instead of side lights. Windows are also in our plans too, but probably a next year project. So my thoughts is that we may get a start this year with paint and landscaping (and MAYBE a new door) and then we can do some other upgrades, like windows, next year. It's worth noting that the top windows do a decent side trim around them already, but you can't really see it in my original pictures because the trim and stucco are basically the same color. If the trim were painted a bright white, it would stand out a lot more, especially against a darker stucco color.

Friends have the Charcoal Gray on a West facing wall. They have had to have it replaced as it faded within the first year. Has done so again, so they are painting that wall. I'd be tempted to with light on the color.

the best way is to have them send you some samples (that's what I did) so you can see in person w/your paint color go for a charcoal, slate gray, or dark gray. since you home is blue, you could use the gray w/the cooler tones like silver, blue/gray, pewter, slate. You probably want to stay away from the brown tones or warm grays for example, Driftwood is more brown compared to the pewter. I think this is pewter this is georgetown gray. I don't care for this one w/your blue. plus, it has a lot of variation. you want something that has more solid coloring you need to narrow down you selections to a type of shingle, and then get some color samples of those.

Also…because you have a storm door on your door, it is obscuring the color and muting it. Another thought…in the mock ups, people have provided you with better sized shutters. Measure yours. They should each be HALF the size of your windows so that they would appear to actually cover them, if closed. A bit wider and a bit taller might give them more presence. Just a suggestion…