my very first thought the shutters have to go, my next thought was the color of the shutters is a great choice for the paint color lol. a dark gray. Or you could do a sage green. id not stain the shingles but clear coat them.

I think working on the landscape will also help the front of the house.

Is the back yellow? I'd pick a slate blue for the house.

When we had our cedar shakes redone, they recommended leaving them to weather for a year before painting or staining. We did ours in a dark grey called Forest Black by Dulux. I love the colour.

Dark grey top looks too heavy. Consider leaving shingles natural, add grey-green shutters and door. Do sides and back grey-green. Then landscaping.