What a fantastic architecture. When you do the brick, if you stain it with masonry /concrete stain you won't have the same issues of maintenance as with paint. They will spray it evenly - through you will have to select a deeper color - either taupe (brown-gray) or a straight charcoal. Love your windows and the classic angled railing. I think a dark gray on the siding will make the orange brick jump even more. What bothers me is the white (railing, fascia, eaves) juxtaposed with the earth toned stuff. So I would recommend camel tones - for the siding - something like http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6108-latte/ and the hopsack next darker tone for the garage door. Use the lighter tan for trim that is now white - http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6107-nomadic-desert/ Use the darkest tone if you are painting concrete steps. If you think you will stain your brick charcoal, then the white eaves and trim are probably right, and you may not want to paint it tan now and then go back. If your brick were charcoal, then I would block out the rest in grays and blue grays - leave the white eaves, but take the railing and posts charcoal too. A blue gray door - like sw smoky blue.

I would suggest you take out the cabinet that is to the right of the stove and use it elsewhere in the house -- perhaps in the bathroom or dining room with a hutch above it. Then, I would suggest you have someone install a lazy susan cabinet in the corner between the sink counter and the stove, meaning you would move the stove down a bit and have a small cabinet/counter top to the right of the stove. I would suggest you have the cabinets refinished in white and then paint the walls a pastel you like. If you would prefer white walls, then add white-painted crown molding and paint the ceiling a light neutral blue, such as Sherwin Williams Niagara Falls Blue. Then, I would suggest you choose a favorite accent color and use this sparingly in accessories like towels, pot holders, small vases or floral arrangements, and a valence above the triple windows. For a genuine 1940s look, you might have white ceramic square tiles with a rectangular red border installed as a back splash behind and above the stove. If you are replacing counter tops, I would suggest a light color such as white with a beige or light grey vein or striation for some sort of pattern. You might be able to find the same color and design in floor tile OR opt for a wood floor as another poster suggested.

Excuse my duh-ness but i'm having difficulty trying to follow whats going on here. Are these two photos an exact replica of your house and pool ? If not a hasty sketch with dimensions could help a lot. By kitchen wall do you mean the wall behind the bar ? And where is the pool wall ? Are you considering the covered area as being "inside" ? Sorry for all those questions lol Sometimes when you have a design problem you need to turn it inside out or on it's head. If you can't beat it maybe embrace it by making a feature of it : i.e. contrast by having the lightest colored pool surround and a great blue or tile inside and under the overhang, something that will echo the water color ? If you have a great covered area as in photo you'll most likely be spending a lot of time there and it could be soothing to be able to sometimes retire into a darker inside. In my book, 10M isn't small and also contrasting two floor colors doesn't necessarily make a space seem smaller and confined and may in fact even open it up. Could it be that you've thought yourself into a box here ? Sometimes one needs to give it all a good shake up and see how it resettles.

With any post war house built in the 50's the connection from in to out is non existent. Depending on where living rooms are located i would take some of the fantastic windows out and replace them with French doors, or bi folding doors and connect the house to the site. The colour scheme from Karen is perfect to lift the kerb appeal and give it a modern twist. With land costing more than houses these days and the fact that you seem to have quite a big block, after looking at paint colours, opening up the living dining kitchen areas to the outside with a roofed area. Even combining a flat roofed carport which will widen the house to the street making it seem a bigger house, can carry the new look with say an enclosed section for garden equipment, to the opposite side to the house, and if you are lucky enough to have that near the living area it can be used as both car cover and outdoor living. I always think a good landscape architect is worth their weight in gold, to give you a landscape plan, to suit the soil type, your skills level and your preference in planting. Divide up the exterior space to provide outdoor rooms under a tree, paths that lead to some special spot for kids, maybe even a veggie patch with a chock run, and make sure that you use the entire yard, front and back by enclosing part of the front yard in fencing which suits the style of the house, while providing some planting to the street. If allowed a gate structure to blend in with the house, a dedicated pathway with planting each side to the front door, fantastic fencing and consider natural materials like a hand laid stone fence with timber or powder-coated aluminium inserts, to give this house an entry, not sure where the front door is now, so that is not a good look. Gardens always enhance a house, they are never a wasted effort, and if you are not gardeners, make sure the landscape architect knows that and he will be able to select low maintenance plants. All the paint in the world will not give the desired effort that the garden will do to that paint work.