I would not do shake siding IMO does not belong on that house . Why grids in the windows ? Since you are doing the siding and the garage door get those arches squared of for the garag door make sure that door has some glass. I like navy and white it is classic looking. I usually do not like shutters but in this case you have windows that can handle shutters the right size. I would do the shutters and not the grids .What is the design for the new portico? Post that here in a comment and also the new garage door style. and new front door too all posted here in acomments DO NOT start another post.

General concept of Portico. We cannot do sidelights though because the upstairs steps are immediately to the right of the door.

We don't have the garage doors decided on yet. But yes, the arches will get squared.

For grids in windows, most of what I've seen with the colonials has grids, and I do think it's a nice look for this style of house. I also, realize it obstructs view, hence the reason for only the top half. Also, the best view is really from the back of the house (overlooks the countryside), so no grids there. Example below.