Wow, painting the brick would be really unique. Please post a picture here if you do that.

This is what we suggested for a customer with a similar house. I think it would look good on yours too.

Dark James Hardie Siding & Trim, Soffit, Fascia & Gutters in Naperville · More Info

Remove the shutters on the window to the left of the picture window. It looks odd next to the window with no shutters. Landscaping would be a big help. I'm not a fan of painting brick.

I think that your house itself is beautiful. I wouldn't paint the brick.... The brick is gorgeous, and the shutters work nicely with the roof color and the siding is a nice neutral color. To give more curb appeal I would add a rod iron decorative element above the two windows in the middle on the siding, or your house numbers up there decoratively. And I would widen the walk way adding brick in a herringbone pattern on both sides facing the house almost as if it was inviting people to the door. And definitely add some type of garden in front of the windows on the left. I would make the border out of the brick too continuing the herringbone pattern.

I'd deal with the entry first.

Light gray siding would look great too! you could do something like this:

Light Mist Shingle & Plank Lap Siding with Alside White Shutters in Naperville · More Info

I love the idea of grey brick and black shutters! Have you considered adding flowers/hedging for a nice pop of color? I wish you the best of luck!