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.

I don't mind the suggestion above, SW Cyberspace, for your shutters. But your front door should be an accent color that is different from your shutters. You want to bring attention to the front door and not the garage door. Right now, your garage door is getting all the attention. Your secondary door should be painted the same color as your siding so it blends in rather than pops. You could go with a red front door. Then add a wide walkway to your front door. The landscaping needs more work. Those bushes are too large for their location. Post in the landscaping forum here to get some ideas for anew landscape plan.

I love a wood front door, but with the covered front porch, it looks like the door would disappear into the shadows if it were wood or even too dark colors. If your front door has white trim around it then a wood or darker door works IMO. I can't tell from the pics posted if you have much trim around the front door or not. Right now we are getting the black hole effect on your lovely home. Try a lighter, brighter accent color or even a soft color for your front door. What is your favorite color? Try that :) The front door should be the accent color and not the same color as your proposed shutters. ^This one is surrounded by white trim and sidelites so it doesn't recede into the shadows.

Is that real brick? It almost looks like some kind of panel made to resemble brick. If it is real, often they just did a thin veneer of brick on only a portion of the house to save money (as if we'll never see the house from the sides? what were they thinking?) Either way they can be removed/ replaced with more harmonious / congruous siding.... whenever it comes time to paint, not right now. If you do a pergola or new porch, keep it simple and in harmony with modest post WW2 1950s style. Your house is not the early 1900s or craftsman-esque style pictured above, and houses start looking like frankenstein houses when they have too many styles from different eras cobbled together. You should find that a lot of contemporary style will mesh quite nicely with your house - since it draws so heavily from that era. The conventional wisdom is to live in the house for a year before doing anything irreversible, but I dont that applies to tacked-on temporary things like awnings and such. Have fun!