Here are the pictures of the house...

Since you like grays, I would consider doing the following: cut back the tall shrubbery. Paint the the brick and siding on both sides in Sherwin Williams Amazing Gray SW7044. If the siding is vinyl, you should not paint it a darker color, since that will affect the way that it absorbs heat from the sun and expands. Painting vinyl siding can cause it to warp. If it is vinyl, keep it white. Paint all of the trim white. Paint the door on the left side of the house white so that the side entrance is less pronounced. Use a latex concrete stain over the front steps to make them look newer and fresher. I suggest Felted Wool SW 9171 (2 shades darker than Amazing Gray) for the front steps. The last thing to do is to paint the front door in a color that makes you feel good every time you drive up to the house: whether it be blue, black, red or whatever. I suggest waiting until after the house is painted before picking this color, so that the overall look of the house helps to inspire your selection. Buy some big beautiful light fixtures to go on each side of the door to replace those old fixtures.

Hey Beth, you commented on my post about our lake house...if you scroll up to May 2017 post you will see our updated pics of how we finished it off! We actually tore it down and built new on the exact same footprint!

I’d probably do a white base deepish brown trim. Nothing too dark. With light blue accents ( front door. Maybe shutters...)