I vote for first option (the darker option). If you plan to paint anything, you might consider that ligest tone in shingles or something close.

estate gray

I’d go with a driftwood or something more brown. These three pic are showing what you house could look like with the roof color change, then with simple landscaping and then if you had awnings above windows removed.

I like the darker charcoal color but, I dont like all the variegation in the picture you show. I would like it a bit more solid looking. Brown would work too, if its dark enough, and again, not a lot of variegation.

I like Emily’s picture of the dark brown roof and the awnings removed. The awnings are very dated-looking. Does the house face west or south and they’re necessary to keep the sun out?

The darker-colored shingles provide a strong contrast with the current house color. That’s a good thing. I suppose you could go with the darkest gray color, but the brown looks better with your yellow/green.

I don't plan on removing the awnings. My house is south-facing so there is a

benefit to keeping them (cooling costs). A lot

the houses in my neighborhood also have awnings. They really don't bother me. The chimney will be coming down though.

The awnings dont bother me either, although the ac unit in front does. I am assuming, there is no other window on the side, that you could move it too. Why are you removing the chimney? Unless its necessary because its in bad condition, I would leave it. You or someone else may want to have a stove like a fireplace, or some other type of heating unit, some day.