I don't know if you've chosen your shingle color yet, but I know how you feel. I felt very apprehensive when picking out my shingle color. I had the look of our home in my head, and it had a dark roof, not black, but dark. When picking my brick and mortar color, NOBODY agreed with my selection except for my husband. The supply company even told my builder that it was NOT a color of mortar that was ever used with my brick color. After that was over, then there was the shingle selection. Apparently noone agreed with that either, except my husband. Everytime I picked a dark color, someone from my building team would hesitate. Finally the project lead suggested Autumn Brown by Tamko at www.tamko.com. It has a combination of browns with a chocolate brown, which is the color of our mortar. The shingles went up on the house today, and will be completed tomorrow, and the color is perfect for the house. I was concerned, even after we ordered a sample and set it next to the brick and mortar samples. I also used www.colorplan.com to give me a clue as to what colors might look good on the roof. I hope you are pleased with your choice. Here is a link that might be useful: My home build blog

My current home has clapboard-style vinyl siding. The neighbor has the Dutch lap. Over the years I have come to prefer the Dutch lap. I almost had mine replaced, and I would have done the foam reinforced Dutch lap. Straight vinyl clapboard has a tendency to wave. Especially over long expanses. In our neighborhood almost everyone got a new roof in 2008 after a bad hail storm. Those that chose black regret it. It is too stark. These are mostly traditional homes. Go with the charcoal instead.

I think the green might be limiting if you ever want to change the shutter color (although like you, I think the color is perfect.) I would do the dark grey.

What actual color is your brick - pink like the second pic or more orange like the 3rd? I would get a sample of 2 and 3 and 4 to see which looks better with your brick so you know what it will look like. To me, Weathered Wood is a good choice with your existing colors but you need to have a sample in hand to see how it looks. This color above is the CertainTeed Landmark Weathered Wood as shown on my computer monitor. Best to have it in person. This pic below is of the Driftwood color from CertainTeed Landmark. Very similar to Weathered Wood. I'm sure the color difference would show up (more pronounced) if you have the samples.