I am a fan of Hardie materials. We have had some on our house for 20 years, and it still looks as good as when it was installed. Installation is more expensive than for wood products IME, and i will let you compare materials cost. In that same time period the other parts of the house have been painted 3 times. I would go for shingles rather than vertical siding. I would change out the garage door to something more attractive and in a color you like rather than matching the house to the garage door. I would go for a gray or brown in medium tones as suiting both the architecture and the wooded setting. Some judicious pruning may be in order, though I wouldn’t go as far as Jan Moyer. I do agree that the privacy fence as currently installed gives the house a feeling of being barricaded from the road. What is its purpose, and could that be accomplished with a more open fence along with carefully chosen plantings or with curtains of some type?

You have a lovely house but it looks chopped up. The two parts, each with a door, kinda makes your house look like a semi-detached house. I think once you decide on your windows, you should try and make this house look more cohesive. Perhaps changing the colour of your siding to match closer to the grey shake colour and not white like you are thinking. I would definitely play down the door on the right and make it disappear. Perhaps you could achieve this with landscaping and really make your actual front door be the focal point. Maybe plant mid-sized shrubs and a couple freestanding trellises with climbing plants so it's blocked off from the front door and hidden or partially hidden from the street. It doesn't look like you have a sidewalk to the door on the right which you could add. I think your goal should be cleverly disguising the utility door so your actual front door is the focal point by unifying styles and colours and adding landscaping.

I agree about the number of materials. I would stop the brick at the bottom of the first floor framing. Two kinds of siding are OK if one is higher than the other and consistent. You would get a better idea of what the house will look like if you got rid of the computer fill patterns. Do that and lightly add some color with Prismacolor pencils. The colors only need to be symbolic, not the actual colors. You're only trying to see how the elements work together. Its a traditional house so let it be traditional rather than modern builder. Without a 3D model you won't know what it will look like until its built.

If your lot permits you to turn the basement more east than southeast, consider doing that. Alternately, consider adding a concrete block retaining wall on the east side to expose eight or more feet of the east side of the house to add a sliding glass patio door to enable the morning sunlight to enter the basement. Like the blue and white idea. Instead of a hip roof on the left and right side, you might consider left and right gable ends -- more headroom in your attic and potential for better insulation and air flow options.