Thank you Summerfield! Sorry it's taken me so long to get back. We've been out of town for a week. I am a mother-in-law now! After the wedding, we went to Kentucky, Tennessee and Arkansas. Along the way, I looked at houses, and noticed some differences in houses in other areas. In my area, most of the houses that are about the same size as mine, have siding above the brick done like mine. There was a house in St. Louis that was almost exactly like ours with brick color, long front porch, and shutters, and they used a dark sand colored paint on the siding, and white on the trim, with darker brown on the shutters. It looked great. The house was also about the same age as ours, but the colors made it seem a lot newer. Most of the houses in Kentucky had brick all the way up the gable. Tennessee had a diving board between the brick and the siding on the gables, like in jakabedy's first photo. While I don't think it's possible to add a bigger face board there, I do think it will work to just paint the one we have in another color, like in Summerfield's drawing. It would help if the board were wider than the siding, but since that board can't be changed without redoing the siding, we'll just have to see what difference the paint will make.

I can't even see the house. any way you can get some pruning to take place? Major pruning? Honestly, the house could be chartreuse and no one would ever know! If the stone work is staying, pull some of the tones from them. for the door I'd do more of a reddish/lavender or gray/charcoal. Blue is just not going to work w/the stone. (unless it's a blue/gray) are you sure you don't want to wait until you get the new roof?

The trim I was thinking of is the fascia board for the black. Plus the front door, like the inspiration pic above. Black and white is classic. I don't think you need black window frames. The windows themselves will appear black with the siding painted white just like your windows appear black now with its current color siding. Landscaping will finish it :)

I feel bad when someone posts and no one sees it until months later--it looks like we were ignoring you. My sister's house is perwinkle blue--I think your house would look great that color.