My opinion is that the darker charcoal gray is going to meet your stated objectives the best. Determining which would look the best would be harder to do. The dark has more contrast the light has less. I think it would come down to what would look best on your particular house and on individual preference.

The living room trim doesn't look random because that trim is throughout the main level except for the master bedroom. The oak is what seems random to me because it's only there in the hallway, though in multiple areas (banister, wood column that's hiding an old chimney, and built-in shelves next to the column. The door stain is kind of random also. The whole has random elements because the previous owners really went to town with "upgrades", but they choose a lot of different finishes, so the main living area has four different wood colors between the door stain, walnut trim, the oak, and hickory cabinets in the kitchen. Maybe I can stain the oak to match the walnut trim at some point. I don't think the entryway shelves will look cluttered because there will be baskets on all of them to hold shoes etc. DH didn't want cupboards, and the kids would probably break doors on them anyway. It's hard to figure out what will eventually go and what won't. There's a whole lot that I'd like to replace/redo, but DH doesn't really want to do any of it, so... I'm leaning toward keeping the beadboard but painting it the wall color. I had a designer come today and she said beadboard would look ok if it was painted the wall color. Also, the dining room, which is visible from the entryway, has a narrow strip type of wainscoting that is reminiscent of beadboard, though stained walnut color, so I don't think it will look too out of place.

I did not provide enough information and also my photos were not detailed enough to show that the actual (brand new) WINDOWS (from Window World) are NOT the same color as the old painted wood surrounding them. We think it will be impossible--and not look particularly good--to paint the wood to "match." They are a shade of beige, but it appears to have a slight undertone of green to it. We wanted to keep the shutters to add more color, but I get your point and appreciate your feedback!

@cat_ky I have definitely done a 180. We've narrowed it down to charcoal, pewter, summer storm, and heather stone. Since our original roof was also in the grey family, I don't think we can go wrong. The neutrality will give us future flexibility. In addition to changing out the exterior front and garage doors and adding a colorful plant bed, I think we may also consider ways to refresh the front windows so they are gridless and the fascia trim color in the near future. It may not be the light and airy style that I do love; but, hopefully, it will still look updated. If we feel like we're missing something, dare I say changing the brick color is an option. Everyone has been great! My hubby is happy that I've seen the light (lol). Thank you so much!