Pretty color! In your original photo it shows the door entry area heavily shadowed so you could get away with that shade or that shade slightly brighter. Really though, I'm not a paint expert so you will need to get some paint samples AND sample boards. Most people have to go through a few samples taped up in the entry area for viewing in different lighting before they decide. When I was remodeling my latest house I wanted a certain orange shade for my door but with a tic of red and a tic vibrant as the door was way back and under roof. I bought a zillion paint samples before getting fed up. Then one day I was in Homedepot and happened by the Glidden paint chits. I saw the exact color but thought as with the other brands the painted paint would look nothing like the chit. It ended up exactly like the chit! I will forever go to Glidden for my door shades ( mostly) as the color on the chit is the color you get. I have them mix it in Behr's best paint though. There is a paint expert here on this forum that shares her very detailed knowledge of the science of paint. I look forward to anything she posts. Keep ready on this forum and you will learn a lot .

Looks like you have it thought out. I would suggest picking your roof color before you pick your paint color. Paint color is much easier to change over the years. Personally, I would pick a very neutral shade such as grey or black (like you suggested). This way you have many other color options for the color of your home as time goes on. You can find a beige/grey to soften the red in your brick. Versus a cooler grey (Wow that looks really blue next to the top one- but when by themselves, they both look more grey) It will be nice to see how your roof impacts the look of your home over the course of the year and throughout the different seasons. I am not sure where you are located but a north facing home, in the northern US, a grey will take on more of those blue tones. Yes, I would make those attic vents blend in. I am not sure that I helped any. Good Luck!

I would try to convince her to 'uninsist'. That seems to blend into its site in its earthy color. A plus to my eye - And I am also in the PNW. She needs landscaping. My own ground here on the coast is too wet for spading and preparing new beds in January. And please note that the house behind and to the left are white. This house also white would be redundant.

I think it best you rethink which of your wishes is most important to you, because doing all is an expensive project.