I think I would also be like you and need to paint while the house is empty. I think the suggestions above are good ones. Also look at Revere Pewter, a Ben. Moore color that is very popular. It's a warm grey and you can do a search and find it here. Also, a neighbor of mine just painted her living room and hall a color called Dune Drift in the Seaside Collection by Valspar paint, sold at Lowes. It's a very calming color that is a neutral greyed green. A great Ben. Moore color that a few friends used and I love (and wish I used it in hindsight) is called Bamboo Shoot #1529. The other colors on the same strip as this that are deeper in color are also beautiful (Ocean Pebbles). My daughter just painted her bedroom BM Coventry Grey,a beautiful grey (cooler grey with a trace of blue). She says she feels like she is living in Nantucket. Beautiful with white molding. I have seen photos of most of these colors on this site. I don't like how the colors show on My Perfect Color, so don't check them out there. Sorry, I don't know any specific colors by Behr, but they will match anything because the color formulas are in their computer.

Keep the shakes! They lend your house character and texture and are fitting for the style. I think it would be bland without them. However, that doesn't necessarily mean you need to keep them stained. Paint is always an option. White is always a classic choice and never goes out of style, whether you keep the shingles stained or not. Greys have been around for some time now and may begin to look dated sooner than you'd like. One idea that I have been loving a LOT is to go darker. Just an idea! Best of luck!

Thank you @houssaon. We do love this house and have worked on restoring/renovating the interior and now we're moving to the exterior. The landscaping and new front entry steps are the next big project to begin this summer and we're very excited to have it feel more cohesive and appropriate for the house and lot. We have thought about adding a sidelight, but the front door is actually original to the house and has such amazing detailing. It's in great shape and we're hoping to keep it if we can. We'll paint it and see if we want a door with a sidelight - I love the one you posted. Thank you!

I went and looked up your previous post on color. I agree with above that you dont need to match your pavers, however, you dont want your paint to clash with them either. I think the paint you had on the house on your original post, or something very close to it, is a better color than the dark charcoal you have now.