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

You've got shakes and brick on the front and, what appears to be, vinyl along the side. Was the house built like this in the 1980's? If so, then just paint it all one color. Or remove the front brick and shingle and re-side. Or just re-side the whole thing in fiberboard if your budget allows. If you want to play with the roofline, then that's going to require some input from a professional (like an architect). I think painting it all one color is the answer. However, I am reading a book on Bungalows and Craftsman homes and they painted the upper and lower floors different colors specifically to make the homes appear lower and wider. So maybe that's an option--but you don't have a visual divider between the 2 floors on the sides so, again, I would just go with all one color. You don't need to make it look less like a dutch colonial, you just need it to look like the prettiest Dutch Colonial. You need nice landscaping.

Thank you so much celerygirl for these visuals! This really helps. I think we are going to go with the two tone.

I sort of like the colors you already have. I would add a nice bright color to your door, and some nice bright outdoor furniture to your porch, and brand new landscaping. The steps are so wide, you can easily add colorful pots to them., too. Is that just a patch of blacktop in front, or is that part of a circle drive. If its just a patch remove it. If its part of your circle drive, then have it resurfaced. I cant see the front yard in the pictures, but, dont forget it, when you do landscaping.