Gorgeous! It's supposed to be earthy so I'd stick with browns (I never say that! but it works here) or greens. Maybe something sagey?

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.

Dark sky compliance is much appreciated by professional and amateur astronomers as well as local wildlife. I suggest picking a compliant contemporary style fixture you love for the front door area, then other fixtures from the same manufacturer's line for the rest. You can search " dark sky lighting site:houzz.com " in google. This article may be of interest: https://www.houzz.com/magazine/landscape-lighting-that-doesnt-wake-the-birds-stsetivw-vs~76419325

Yes, the plants are a constant work in progress with the shade and the sloped yard and deer that devour everything. Once we got the pachysandra growing densely that helped. Deer don't touch the boxwoods. We have rhododendrons, but they are high since the deer trimmed off all the lower growth. We had some rot, but the painters brought a carpenter who replaced all the bad boards. We've also had to do control for wasps and ants. Keep ahead of the bugs. Figured out we had insects when the woodpecker started on the siding! When budget allows a more contemporary front door would be nice, plus change the light fixtures, and stucco the chimney.