I would remove the shutters, change out the front door, and go for a roof close to the current color. I wouldn't go gray or black unless you plan to paint the siding.

I like the black, your house is far from ugly, and reworking a bit of landscaping will work miracles.

So early fall and then the covid19 and we are finally back in fix up mode! We will be getting our roof done shortly and are replacing windows. We are doing vinyl replacement double-hung windows but I need some suggestions about grids or no grids? What do you think? Thanks for any suggestions. I removed the full window grids we had to see what top grids would look like. Also, the dormer roof has a minimal slope and our roofer says not to use shingles on it but a cap sheet to match the roof color - what do you think about that? And, last but not least, what color for the exterior and gutters? Thanks everyone for any input. We are getting landscaping redone in next week or two and already have decided on that. What style would you call our home?

I agree with Design Girl - if you are not occupying the house yourself and are renovating for resale only - I'd use the Sierra Gray. As Design Girl said it is the most flexible when matching up with siding, etc.