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.

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=]

Hi Please disregard the attached plan (not part of this house), sorry for confusion Matt

Sorry I am so late coming to your site - you are an inspiration to all, homeowners and advisers alike. For your planting advice, I suggest you call Merrifield Garden Center to see if they will come out your way. They currently have wonderful garden centers in Merrifield and Fairfax (both in Fairfax County) and a new one in Gainesville, but they may come further south to wherever you reside. (www.MerrifieldGardenCenter.com) Even if they don't send designers to your area, they are worth a trip to see their huge selection for a day of pleasure and inspiration, or to pick up some plants. Most of my clients are in the Fairfax and greater Washington area, but I am currently living out west below Front Royal, VA on the Shenandoah mountainside - wonderful views. cascio.offsite@gmail.com