I love a mint green siding, really makes the house light and airy, and will look nice with dark chocolate brown window trim. I would do the door trim the same dark brown color, but keep the soffits and fascia a lighter cream. Try to find a shingle with speckles of color in a dark brown, but with some charcoal gray to it as well. Here are a few examples to look at. Or you could go with earth tones for the siding - a light tan would compliment dark brown trim well.

You are discussing some pretty big, expensive projects, which done piece-meal could cost you more & not come out well. I would suggest you contact some contractors who have a good reputation for doing renovations, or even an architect to bounce ideas off of before beginning. Your house looks fine to me, except for 2 things which stand out: tree closest to stairs is overgrown & should be pruned back as it is hiding stairs & part of front of house - same for tree at other end. Can they be blended in with current hedge? Ask a landscape designer. I like the brick & the colours. The top half of house needs something to balance it better, and I am not qualified to make suggestion: an architect or general contractor would be..

I don't mind the brick--is it a facade material or slump block? Is it naturally white, or has it been painted? I often hear of staining brick or block to the desired hue, perhaps this is the answer? Posting a recent pic of the work being done would be helpful. It sounds like you have already made a lot of the material decisions, and as such, the advice you receive going forward has limitations. I would have preferred some means of Hardie Plank instead of stucco, as I believe the horiz. separation btw. the laps can add interest. I think stucco was a rare occurance on this era of home and I feel it is somewhat monolithic, short of adding a stone wainscot, which competes with the brick. The maintenance, however, is minimal, and I am guessing that is why you chose to remove the siding and add it? Would brown be a color that absorbs alot of heat in your area, or does the ocean breeze take care of that--is there a better lighter colored option to consider? In terms of the entry, I would like to see some mods to the roof line that would draw your eye to it, such as raising the ridgeline to match the major roof, and as you bring it forward to the entry door, stop the overhang above the existing low roof overhang. This would allow you to add a transom window over the entry door, and to create more volume in the foyer itself. You have a great home to work with. Happy Houzzing.

So - my suggestion to wrap the front (back to the porch wall / front wall of the house) and around the end to a logical conclusion in back with shingle (staggered edge shingle) is in the same vein as putting stone on the gable area . . will give it a different texture that reads cottage. I love the idea of a blue green entry door on a yellow cottage with white trim . . . even go to a sort of honey tone to echo the warmth of the natural stone you have in the landscape . . .If you want to keep your shutters, perhaps try the little window with one single full shutter hung to the right of the opening . . a bit more charming / distinguish it from the other windows . . that will echo that area as an accent and the window on the porch without shutters needs them too . . . all or none . . charcoal gray shutters in the tone of the roof could work on yellow and white .. . Here are some images for inspiration -You may want to incorporate shortened fake corbels under the white gable vent in a trio - pro wood market has some - just looking at your stone planter beds, while they don't really have enough charcoal gray tones to repeat the rooftones, they do have a lot of gold, red and persimmon tones. Local stone I bet . . maybe add some gray or gray cap to it, and have them buried / dry laid so the top is flat like a sit wall . . . perhaps eventually lay some gray slate on your porch and stair? Plant a row of flowering small bushes on each side of the path to make a row ... you have a lot of charm potential here. more of a cobblestone facade with a yellow door - great trim details at door - sort of would match your existing terrific window trim detail great blue green at door tho house is grellow (greeny yellow)