I need to see a close up of the stone. The shutters are all wrong on those double windows and IMO on the house at all.

Tracee my suggestion is, if your painter is dead set on using Dunn Edward’s paint then look at DEs colors only. I have seen color matching go horribly wrong even though your painter will swear by it.
The other option would be for you to buy and provide the SW paint yourself for your painter to use.

On a previous house I had picked a beautiful color that was on another house in the neighborhood and insisted that my paint use Behr paint because that was the brand the paint color was. Well he used DE and paint matched and the house came out looking like an army tank.
Dunn Edward’s is a good company just an example of what can go wrong.

I think Repose Gray might be too dark. Your stone is very light. If you use something on the rest of the house that is much darker you will accentuate the different surfaces. Unless that's what you want, I would first of all remove the shutters for good and then try something close to the mortar color. The roof trim could be done in the darker color. I agree with Ron that you should only be looking at DE instead of trying to color match. Get chips that are close to Repose Gray, but lighter, and paint a sample board (about ten square feet) with it. Then you can move the board around and look at it on all sides of your house. You can't get the same effect from a paint chip, and you don't want to waste your money having a contractor paint your house a color you don't like. If you end up wanting it to be redone, chances are he already has another job he has to get to, so a redo might not be as easy as you think.

Photos of the new roof?

Thank you for your feedback. Here are more pics. These were taken just now at about 10 AM, west facing home in southern CA.

Charcoal shingles