I wouldn't paint the brick. I would choose a siding color close to the mortar in the brick - light gray. Agree to remove the shutters. Paint the door white. Maybe even paint the stair risers white to brighten that area

Are you saying that your house is on Cape? I have never seen any structure here which looks like yours.. I would suggest white clapboard and painting the brick white, as well. No shutters, for so many reasons....vinyl, do not fit the windows.

White on white will meld both sidings.

I think it was originally a Cape but shed dormers were added on the front and back. I also don't think you should paint the brick. There is nothing wrong with yours and it's not that unusual to have the second story be a different color than the first. I also would look at grays for the siding. Hardie has a selection of prefinished colors. Hopefully one of them will suit. The most unattractive feature of your house is the window on the second story in the front. The half moon over it is odd, and the window is too small for the expanse of exterior wall. Since the interior configuration is a major determining factor in whether you can change this, I don't know if it is an option to change it. But if you're residing, that is the time to consider such a change. Two or three separate windows spaced across the facade or expansion of the existing window so it's wider (three windows instead of two) would improve the appearance of the house.

What is the paint color of the current siding?