I'd do a vertical board and batten look on all of it, or a cedar shake look like the Nichia shakes on all of it. Or just keep the stucco look and emphasize the French Country details. No horizontal lines with that roof as they'll emphasize the width of the house and make the roof even more prominent. And I'd reframe that tall section to have the roof "wrap" around it as well. Then do the windows as dormers and add some dormers to the main facade. That takes away from the overbearing roof look and gives additional light to the interior as well. I'm not at all a fan of using something completely different on different sides of the house. It's a look that says "I couldn't afford to do nice stuff everywhere". Even just adding a few dormers will make that roof more charming.

We had a hailstorm last year and had to have our roof replaced. Where we live several houses were having their roofs replaced and our HOA calls for you to have the color “weathered wood”. We started noticing lots of roofs being replaced and the newer shingles are very speckled looking! a house that has a lot of variation in the brick can really look a little crazy if the roof is speckled also. I would just be really careful picking what looks like architectural shingles using sample pictures. If you call the roofing supplier or your roofer they should be able to give you addresses of the colors of shingles you’re interested in so you could actually drive to by that home and see the shingles on an actual home. We found it very helpful and the color “weather wood” is very different looking across different brands of roofing. We chose Malarkey brand their Legacy line in “Weathered Wood” color upgrading to the class 4 impact resistant shingles. you also might check with your insurance company because we paid a little extra to get the class 4 impact resistant shingle and we get a discount on our insurance. Just a few things I learned while picking Roofing last year!

I don't think board and batten is the right style siding for your home. You've got too much going on with all the roof lines and uneven facade. What you've mocked up is appropriate and uniform, making the house look more uniform than it actually is. I love the mock up you did and I think the windows are appropriate for the style home. I wouldn't do a bow window, but a regular one. Bow windows are dated. I like your color scheme, but fear it won't look great with the brown roof. If the roof will need to be replaced anytime soon, then go for it. If not, you may want to look at other color options with a brown roof. A deep blue gray could look nice. This could be helpful in picking a color. https://www.kylieminteriors.ca/how-to-pick-exterior-paint-colours-in-5-easy-steps/

I'd confirm available colors in each brand before making a decision - we were going to go with Mission Brown, which per the website is available in our area, but due to Covid, they had reduced their colors down to a handful. This was 4-5 months ago so things have maybe changed. Good to know before you get your hopes up as we did. We ended up with Weathered Wood and we like it a lot as well. Before: After Good luck!