Here are a few photos of my house where I photoshopped a render/mockup of what the white walls could look like. FYI, the dining room windows with the black wood blinds will be replaced with white cellular shades (the dark blinds make it so dark in there). I am also playing around with the idea of doing Kendall Charcoal on the window trim, which you can see in the office render. I like the baseboards being the same white as the walls, but not sure about the windows, although the dark trim around the windows on every window might be a bit much. Any thoughts? Do you think white walls and white-on-white works for my flooring, etc?

Love your inspiration photo. Can you remove your storm door or replace it with a full view one? Painting your door won't have much effect if you can't see it!

Your roof is brown and it's very visible from the front, so you're going to have difficulty getting away from it 100%. That brick isn't bad, we've seen a lot worse on this forum. Lighten up the dark brown elements on the facade to something similar to BM Smokey Taupe 983 or Stone Hearth 984. Then cut the tint by 50% for the area between the windows. I can't promise you Smokey Taupe will be the right color because it's difficult to get exact color matches looking at colors on computers. But Smokey Taupe has an LRV of 55, which means it's substantially lighter than the brown. It also is somewhat gray, so it would give you a different look. The biggest bang for your buck would be a substantial investment in landscaping. What you have is simultaneously sparse and overgrown. It's probably been a while since any effort has been expended here. I get it - DH and I don't know much about plants. Engage a landscape designer for a plan and DIY part of it if you're interested and able.

I like the idea of painting them a color that contrasts with the trim. If they are painted the same color as a trim, when they are down the whole area will read as a door and not a window. I'm claustrophobic so that would make me feel really shut in. I'd prefer the robins egg or another pretty color that goes with robins egg. If that is not a concern of yours, I say go for whatever you like. Your home is really stunning, the ceilings, the rim. Lovely. Glad you are experimenting beyond greige.