I am probably too late, but I would think about a soft olive green, rather than a sage. I think the warmer tones of the olive would be nice in the shady space, and with a red door and warm white trim, along with the roof color, would be a wonderful combo! Have you considered adding simple trellises on either side of the lone window on the left? I would be nice with the cottage feel of the home, and would give some visual weight to balance the three windows on the other side. Paint the ceiling of the porch in a light blue, and change out the railings to wood ones. A charming cottage! Your current home is wonderful, and I can understand you hating to leave. But down the line, especially since remodeling is your passion, you will have something even more amazing, I am sure. For now, the cottage may feel small, but will also give you a sense of coziness and security that could be an island of peace in the storm.

Has your architect completed the new elevation design yet or are you bringing ideas to the architect? I assume you will be using one if you are removing the roof and putting on a third floor so you get the best design for your dollar. The house across the street looks great - hopefully when you finish your home it starts a trend in the area.

Budget and building codes permitting, you could recreate your entry. You might ... Remove the first floor roof from above the front stoop -- everything from the brick to the garage. Create a new forward facing gable roof over that area beginning at the ridge of the upstairs -- at least at that height or even above it -- and extending the roof of that forward facing gable to a point at least twelve feet in front of the downstairs exterior wall. About six feet of this will be your new front entry foyer with your front door moved to the new exterior wall facing the road. The rest will be your new front porch. Alternately, you could extend the forward facing gable roof only six or eight feet beyond the front exterior of your home to create your new entry foyer and then add a shed roof with two hip corners for your new front porch. You'll be enlarging the upstairs room on the left by extending the floor of that upstairs room into the vaulted ceiling space above your new porch; then you can move the original window to that new upstairs exterior wall of your forward facing gable. What front door and front porch post style you use will help define/redefine you home. You could also add an arbor across your garage that coordinates with the posts you use for your new porch.

As a few others have indicated, you may be able to get the look you want without painting the brick. Here's a few options that look nice with brick. I know you are planning to paint the doors the same color, but I think raee above was asking about making the actual doors match. I think the one of the right is more in keeping with the age and style of the house. Obviously it won't have the transom but the same kind of door with the 3/4 window would give it some cohesiveness.