This attractive house has three high contrasts already: charcoal roof, red brick, and white windows. Which of those features do you want to emphasize by adding more in the same color range?

Good question...I'm hoping to find a color that goes well with the brick as well as the roof, but isn't too much.

Have you tried an online paint visualizer? https://www.sherwin-williams.com/homeowners/color/try-on-colors

Thanks! I've tried the visualizer with a few shades of gray as well as the Slate Tile. It's hard to tell how true this is to the actual color?

If we got with the bluish/gray color, do you recommend us doing the trim in the same color or a different color?

We will be closing on this house around Memorial Day. Need input on adding curb appeal, exterior colors, and tying in the garage and Sunroom additions. The vinyl siding is not great quality. We think we would like to change siding to hardy plank and replace garage door. We've elected not to paint the brick for easier long term maintenance.
The front landscaping needs so changes too. The house inspector recommended trimming the cherry tree branches away from the roof to deter squirrels from accessing the roof and eating copper plating around the vent. The poor tree looks like it's branches have been trimmed over the years and since the branches mirror the root system I'm debating removing the tree and planting a new tree. Any ideas about the tree?