We rarely get updates on planned projects on GW but I'm thrilled to present one now! We started the process in April 2017. He was understandably reluctant to accept help for months, but we assured him his numerous nieces and nephews wanted to help. We donated money, helped tear out the overgrowth and hired reputable contractors to replace all the windows, put up vinyl siding, new shutters, new doors and storm doors. He is so happy about the changes and has accepted our help. We guided him but he chose to keep the brick and he chose the colors and even the door style. (He likes yellow but immediate neighbor has yellow siding.). We took small steps but ever forward, encouraging him, assuring him and thanking him for the generosity he has shown all of us for 50+ years. I've said before he is a dear and inspiring man. Here are a few before and after pics. Front porch will be replaced this month as weather allows. Thank you all for your great advice and kind words.

Hardi Plank has some pre-painted siding materials that are pretty good. Usually don't recommend vinyl. Try contrasting a Med to Dark Gray along with your Hershey Bar brown, with a black or wood stained front door.

Thanks for responding. Attaching the pictures of both Harbor Blue and Platinum Grey with Storm Shake. This is Naperville, IL. Not much woods as this is a new subdivision.

I suggest you cruise on over to Romabio to get inspired about what you could do to the brick, and decide what color of roof looks good on the product you go with. If it were my new home, right away I'd tear out that fenced livestock yard on the back, paint the deck white, replace the front bay with a triple window in the style of the other two (replacing the resultant damaged siding on the gable,) remove the shutters, and wait for spring growth to see what you have for the landscaping. It is likely I would remove both the pencil tree and the squatty one in front of the bay. Another little job I would take care of would be replacement of the utility style light under the eaves. Move the electric box for it to the right so a new, larger and impressive lantern light would hang above your house number sign, which I would also replace with large attractive individual numbers. If you do keep the brick as is, navy blue paint on your front door could be pretty.