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.

A green roof pairs well with gray and white homes. For a subtler look, pair a green roof with a siding in a lighter shade of green. I think you are on the right track .You have chosen harmonious shades . New paint doesn't have to match existing colors, but it should harmonize. Some general tips are- Green roof - Gray, green, or white house colors. You could use a dash of yellow also.

If you use masonry paint, we could head in a warm greige direction for all of it - not so yellow . .. something that can give you a bit more contrast against the white windows and trim - even 40 does a lot for us . . . what about a blue green gray? You will get a coastal / mod vibe and it will relate to the farmhouse look .. .above bm silver mink http://www.benjaminmoore.com/en-us/paint-color/silvermink and below . . . gilbraltar cliffs . . http://www.benjaminmoore.com/en-us/paint-color/gibraltarcliffs Shingle look siding on the side dormers would be neat to get that cottage mod. . . you can stick with yellow but I don't think it complements the roof tone. With the blue-green grays, the white windows and trim will really pop beautifully. . . You can also go more neutral with a warm gray - greige . . . here's the siding tone http://www.benjaminmoore.com/en-us/paint-color/capemaycobblestone paired with this for brick - http://www.benjaminmoore.com/en-us/paint-color/graystone potential future red windows . . .aluminum pits over time, so if you have just one side you want to try, you don't have to powder coat, you can take a small brush and just do them by hand with latex paint if they are 10 yrs old or more. . . one advantage to gray . . future see [houzz=]

This is why it's always good to have a pro to hold your hand for at least some of the way, (carefully chosen though, check out his/her finished projects, the more varied the styles, the better she/he will be able to understand and adapt to your desires), they can provide the invaluable visual supports too. When it's your own house it's notoriously difficult to see the possibilities, you have it under your eyes the whole time and the defaults shout at you and prevent you being able to see it objectively and envisage the possibilities. you're emotionally involved and emotions always have the upper hand on the brain, so you just keep turning round in circles. Something akin as to why a psy must never attempt therapy on a member of his own family, if you follow me :D As for the façade color, are you sure it needs changing that much ? Once those thick white frames have gone and the new windows nestling more discreetly, correctly positioned and re-proportioned, the aspect will change drastically and be far more streamlined and modern. (the devil is in the detail) I'd also strongly suggest that the wood facing just breaks off around the windows, no framing or finishings. Same thing for all the windows, the small ones too. Entrance : Same as for the windows, that outer frame shouldn't be touching the ceiling, you can try taking that off and painting the door another color before deciding to change it and once again the door could do with setting back a little. You could maybe take that doorstep out while you're at it. Also, i don't know what is happening to the right of the door but i see the concrete steps leaing up and feel it would be good to create another level to make it flush with the bottom of the door if structurally possible. This would tie it all in better and you probably wouldn't need any additional definition to your entrance. Anyhow, as i often quote, i'm a firm believer in " Less is More " , and vice versa of course ^^ Question #4 i can't answer as i haven't really understood the problem And #5 i don't think so, but once the other transformations have been taken care of i think you'll find it speaks for itself. Whatever, it's a very exciting project, the bones are great and i'd love to see photos of progression once you get started.