I'd go with a very very dark brown on both.

This is a recommended color from SW for Mindful Gray…homburg gray. I would do this on the shutters and the garage doors and leave the wood door as is. The two middle windows shouldn’t have shutters as the won’t fit appropriately, but you are not painting the siding and the darker outlines of the shutters will show if you don’t replace what was there. Personally, would like the house with out shutters and would probably paint the siding and garage doors and have no shutters at all.

Yes, replacing all windows but not the arched window. So you think it would be okay to do dark framed windows on the front of the house and white on the back?

any Blue will compliment the orange tone of the brick.They are opposite on the color wheel. I would be creative with the panels in the garage door and entry door. Two different blues in the same family. with a bit of white as a highlight contrast to make it more contemporary.