I would use SW Spalding Gray or a lighter color down. It depends on your neighborhood. My neighborhood has very similar home styles of the same year and is lately going lighter. In the last few months some have even gone an off white. They all look very fresh and clean. Anyway, this chit should work whether you choose one of the lighter shades or darker. Chit samples below do not really look like the color "on" but here it is. They change greatly according to the time of day and go from a warm taupe to taupe beige-y to a warm mottled vintage gray. The Heron Plume is much much lighter in real life and would be a great trim color. This color for the door. Don't be afraid to go a bit brighter than you normally would as that area is in shadow. This door painted the periwinkle above. Could you please post a closeup of the window area in front? And, also a sample of what your new roof color will be?

You haven’t said anything about budget. Change out the siding color starting from the colors in your brick. I would want something somewhat darker than the current color. I can’t see that adding cedar shingles to the top part of the gable ends, leaving the rest as it currently is, will be an improvement. Changing out the garage door for one with windows is a good idea. Match its color to the siding as the white highlights something that doesn’t need extra attention. Widen the walkway so that two people can walk abreast, and make it of more interesting material. Find a garden designer to help you come up with a garden design that suits both your taste and ability/interest in doing the needed maintenance. What you currently have has some evergreens which is good, but there isn’t anything interesting or that complements the architecture. You landscape is stuck in the 60’s with nothing except for your two rows of evergreens and a small patch of some type of flowers.

This thread is some what similar to yours, check out his landscape. https://www.houzz.com/discussions/want-to-paint-the-siding-on-my-home-need-suggestions-dsvw-vd~5699693#24071377

I don't see any new colors that I like better than what you already have. Part of the charm of your house is how it rambles and sprawls a bit, and the eye travels to take it all in, so I would be wary of drawing sharp accentuating dark lines on it. Definitely don't cut down those amazing trees, they make the house look modest, unpretentious and tied to nature, which another part of the charm of the house. Don't get shutters if you don't want them but if you ever feel they'd be an asset, functional ones would be the way to go. Yes, they would be irregular (on some of the windows I would only do one shutter on one side) but maybe you'd never, so.... I think the vast expanse of lawn is very nice for your house. I could see bluebells and wildflowers scattered throughout it, and a low key field of something at the right eide of the house, maybe something along the pathway to the garage (does that get any sun?) Ornmentals and foundation plants might compromise the relaxed simplicity of the scene and suburbanize the look You have a house under the trees in a lake of green.... Might be nice to define the driveway-end of the walk to the front door with a very simple lantern/post marker.