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:

Thanks so much, this is hugely helpful. That glass awning shared is amazing. I will see about talking to a local awning company about it to start. The current awning is actually burgundy, not that it makes it much better :). Definitely agree on the landscaping too and have considered starting with yanking that bush out the blocks the front door, even if we wait on the rest until spring. I never thought about the downspout color being different, and now it stands out like crazy. We’ll definitely have that painted to match the brick. Would you leave the other paint as is? On the door, I also like the idea of having the sides be the same color. What color would you paint it? I wouldn’t mind replacing the door but the side lights are matching to the glass - does that matter? There is also a storm door if that makes a difference. The windows are definitely dated but haven’t been the highest on my priority list to change out - as you can imagine, several things inside look like 1995 too. Thanks so much!

BF - what software did you use to show the color on portico ? Is it something I could use to try to see what color would look like if I painted the lower band house color ? I tried to find a program online but it was terrible — looked so unrealistic. Your picture is amazing !

You might be able to fit one like this below the window, if you take off the cornice trim right above the door. You might have to get new smaller windows over the door. If you do, get rectangle ones not one with an arched light.