There are many shades of black and charcoal, I would try some darker grays to find the perfect color for your shutters. The portico color / door color in the photoshop looks khaki, is that close to your mortar color? If so, you might try soft brown shutters with it. Tall narrow trees/ shrubs for vertical lines between the windows is a sort of dated Italianate look that might not be appropriate for your house or location. Homewood is a great area, I love the Tudor style downtown shopping, that is where I had my first lunch at Zoe's. Great schools, too, which makes your home an even better investment. I like the portico your son mocked up! You might also google pictures of a portico style that projects outward (right angle) from the house instead of upward.......like these A pic of same house from farther back:

I don't mind the table and mirror and can't really think of anything besides art that would fit on that wall. Can't see the table details well but could it be painted? How about red to match your lovely door? What would say "fresh and cozy" to you for that space? Have you thought of a new light fixture? A runner and a larger rug in the entrance could look good. I don't find the clock visible from the door to be welcoming so I'd be tempted to remove it.

Match the window color.

That would be so attractive with the Chippendale railing. Neither of the examples below have deep landings. So unless you want to sit out there five feet should be fine. Are you thinking something like this? Or this?