Update: we've decided to keep the siding on the dormer and just repair and paint all the clapboards and trim. I've been testing colors and have found two gray-green shades I like, SW Retreat and SW Link Gray (same level, just one chip apart). The Retreat is almost too bright and clear when I see it in the sun on my South and West exposure, so I'm leaning toward the Link Gray, but I'm still open to suggestions But trim colors are still hard! I think white is too stark with my dark brick and taupe/gray mortar, but I'm not sure what undertones to look for in the trim. I wonder if a pinky beige would work best with the brick while still complimenting the green of the siding. Or vice versa, maybe a green-based beige? The swath of siding on the right is Link Gray, the little piece midway up on the left is Retreat (they look almost the same in this photo). The corner board on the right is Rice Grain (a green based neutral) and the left corner board and some of the window trim is painted Portico, a deeper pinky beige. I think it might be too dark as a trim color, but I can't tell if the undertones work better. The Rice Grain almost reads white, but maybe if it were all over it would have a bit more oomph.

myfoursquare - Thank you again! It's way easier to see your way than having them tipped up by the windows on the bottom. I really don't know if I like them. I'm kind of on the fence. Hubby likes your pic, but he also likes the white band with it which would maybe be too much. I think we should wait too until I can get to the door. So helpful that you did that - we really appreciate it, thank you!!! jterrilynn - I agree. I'm hoping to get out today to see if any places have any nice pots left. We have so much snow here in Montana that I might just stay home today. Thanks for your feedback. It really helps. dedtired - HA! That made me laugh! We aren't going to do the vents. We did have them before the house was resided and I just got tired of them and was happy to see them go even though they added a little "something" to the house. Thanks for the feedback on the trim. We can't take the door off in this weather to paint it in the garage (it's 6 degrees here this morning why do I live here?!)so it may be awhile before we can paint and post a pic, but I will do it.

I think a sage green would look good … This is the wonderful Farrow and Ball Green Smoke: If you’d like it a bit more formal, a very dark brown: Matching the dark red/rust in your stone, love this: This is Farrow and Ball London Clay, an amazing color that ticks all the coordination boxes … your stone, trim, shakes: Your house colors are so neutral, you could do just about anything. :)

I would paint the entire house the same color. Painting the top darker than the bottom just makes it look smaller. I would paint the windows and trims darker. Black, or another dark color Urban Bronze?