The bay window is pretty unique. Rather than have the siding beneath it concave down, how about squaring it out. Not sure how much this would cost, but not suggesting replacing windows, just squaring out the part beneath the window and bringing it down to the ground. As long as you're replacing half round windows on second floor, I would suggest putting in a rectangular window. Although the area does look "heavy," could you just forego anything there and drywall inside and modify outside when new siding is installed? Can window grids be removed or are they between the glass? Not a professional but I feel the window grids do not 'fit' your house.

Good luck with your project, hope I was of some help. Take care !

Everything depends on what you have the ability to do to this house.
I’d either block the bay window shape with tall landscaping or redo.
The dormers also. Would love to see less angles. But not sure that’s an option now.
The brick isn’t bad at all! Do you not like it??
I’d match the garage door with the front door. And all the window trim black too.
You have a very lovely, nice home!!! With a bit of angles and curves ( which I think are the biggest and maybe only issue)

I was thinking we’d probably benefit most money wise with putting greenery under the corner window seat like maybe a hedge to hide the concave...something that stays green all year round (?)
The half moon window that’s got a crack line in it would need to be replaced and was thinking non grid also. I’d love to Sheetrock them and completely get rid of them altogether (old style). Also, I don’t like the Octagon window. We were thinking to paint brick to get rid of the muddy pink brick and using off white or smthg to have a more cohesive look. I don’t know what to do about the windows as we are having different issues with them. They need some kind of moulding or something?

Should we use a colored siding? Or a hardy board? or stucco?

A neutral gray will look best IMO. I don't see any reason to use a metal roof above the garage. The house is pretty chopped up visually already. I would not add another material. I would give some serious thought to eliminating the arched windows and bays over the garage.

Should you decide to paint or limewash your brick, Romabio makes the best product for this application. If you attempt to use acrylic paint on brick it will peel off.

Maybe your home could be adjusted to look more like this.

I don’t have the software ability to see how it would look with changes. So, I appreciate what you have done with the windows.
This is a sample I’ve tried on a roofing website to see how the metal roof would look and then a finger art of changing brick color. It’s only to show what would be changed. Not exact color. The roof above the porch or entry would not get the metal.

The rest of the roof would be black asphalt by Owens Corning.

I really like your idea on color. It’s not feasible changing out the bays above the garage since we are both retired. I’m going to get pricing on possibly changing the 1/2 moon into maybe a rectangle upper.

What do you think of using a color on the wall between those bay windows to give depth or separation?

I like all your ideas. Whitewashing the house will look great. But I don’t see a problem with the current color. I think black windows with that color brick looks great. And if it’s painting the brick or doing something else I would definitely skip the brick for now. You can always do it in the future.

New Roof

Update - New Roof installed.

We are now getting pricing quotes for replacement windows. Can't decide on what to do as far as color of windows. I'd love the black with no grids. But, the other half of the house would be white. Can't afford to change out everything.