The roof is dark gray, doesn’t really have tan in it. Maybe it’s the photo but that could impact the look. I was looking for a modern look by using the dark gray. It’s a risk though and I can’t get my head wrapped around black trim. I just don’t want to paint it some blah color.

Nice place; great potential. Have you consider creating at least one short (<4') retaining wall to create a level place directly in front of the left wing of the house? Could it be done in a way to create a need for less steps from your front porch? Otherwise ... Because I am prejudiced in favor of usable porches. I 'd want to start at the chimney and create an 8' deep deck over the garage entry and wrapping all the way around to the left front corner of the right wing of the house and then continue the same floor level all the way to the left corner of the left wing of the house with a shed roof front porch roof with a forward facing gable over the entry door above the top of your front steps You could always add a roof over the deck later, extending the porch roof over the entry. Put a hip corner in the porch roof on that left side.. Consider having the left side of the porch even extend beyond that left corner of the house by 4' or even 8' and wrap around the corner enabling you to easily add steps toward the back yard -- or even a wheelchair./baby carriage ramp aimed at the back of the yard if this is to be your forever home. I would definitely NOT cut/scar the front yard with a sidewalk straight forward across/thru the front of the yard. I'd begin the landscaping by leveling a place along side the driveway beginning at the garage all the way to the road and put a sidewalk there. I'd add a retaining wall above the sidewalk -- taller (4' or so) near the garage -- and where I transitioned from the taller retaining wall to a shorter retaining wall on the road side of the lot, I'd have the sidewalk create a "C" curve from the beside-the-driveway sidewalk to the front porch steps, with NO steps in that sidewalk. Between the "C" sidewalk leading to the porch and the road, you'd only need a shorter retaining wall above the sidewalk to keep the dirt off the sidewalk. You could curve it just before you get to the road to create a level walk space behind your mailbox and create a planting area as the wall ends. Even if you don't extend the porch/deck around the right three story part of the house, the rest of the above should work. If you do add that extended porch/deck, you could also add steps leading to it from the driveway/garage with the steps aimed at the back yard from the deck/porch beside the chimney.

Your house is adorable! What kind of look are you going for? I like the siding color with the stone and the door color as well. If anything stands out to me, it's the wood posts as they don't relate to anything else. The updated landscaping you are planning will go a long way!

The white looks fine. If you need to paint, paint, but if you can wait a few years, do. If the roof is green metal, keep it. If it is green with moss, kill the moss. The side door will look a lot better if the drainage of the gutter is not over the door (try a rain barrel) and if it were painted white to match the rest of the house. The door needs to be cleaned, too. Your landscaping looks like a jungle. I'd imagine you have some chosen, planted (by previous owners) shrubs that are way overgrown and some weed species that planted themselves. You need to figure out what you have (hard for me to tell), what you want and get rid of the invasives. I can't really tell, but I bet you have some sumac (which can be pretty and is native, but if that's what you have, is way overgrown and possibly too close to the house) and some Japansese knotweed which is invasive, although pretty when in bloom. To sum up, I'd move the downspout, clean the door and paint the side entry and tackle your jungle as the top priorities.