I picked up some paint chips yesterday. The 'cream' is Valspar Eddie Bauer 'Craftsman White', and I guess 'cream' isn't the right term, but it is a very warm white. The color we like for the living room is the same line 'Calico', kind of a brick red. We plan to do the typical tall Craftsman wainscoting, more than halfway up the wall, in the living room only. This would be the Craftsman White. On the other end of the house, in the kitchen, we would like a soft gray. The Craftsman White seems to go better with cooler grays as opposed to warmer grays, at least to my deficient eyes. It certainly is doable for the kitchen cabs. That leaves the DR in the middle. Is there any way to transition from the red LR to the gray kitchen? What kind of tones should I be looking for? The colors grouped with the Calico sample went to a brownish gold, and then a lighter gold, but that's not where we want to go in the kitchen. BTW- we are not married to the red LR- it was just a thought. We could work backwards from the kitchen, starting with the gray, and going to?? Another question- If we go with the very warm Craftsman White for trim, what color would we use on the ceiling? Try to match, or go with a typical flat white? There will be a fairly large crown molding. I really appreciate the help. Both my wife and I are pretty color-challenged. At the paint store, they all seem to be 'yes-men', agreeing with whatever we are looking at, rather than offering useful criticism. It's no wonder our old house was just white throughout! One thing that gives us fits is how much the colors change depending upon time of day, weather, and the seasons. We are out in the woods, and the colors look quite different on a cloudless winter day than they do on a rainy, green summer day.

I really love the look of wood and I would keep as much of the wood as possible. Your house has lots of wood, and as best I can tell from the pictures, the woods mostly agree with each other. Your fireplace wall is mostly overall a light warm pink. Your other woods look like they have a warm tone as well. Even your dark doors have a warm brown with orange highlights. Have you thought about going warmer with the color for your walls? The wall and ceiling colors need to accent the wood beams, wood flooring, wood railings as well as the wood doors. As much as I like the modern gray/white look, I don't think grays do as much for wood as other colors. Why be tied to white trim? If you find a warm color you like, there are other colors that the paint company suggests for trim and ceiling that accent the wall color, which in turn would accent your wood. In one of our homes we did the unthinkable by experts. We stained our poplar wood trim and wood doors with a dark antique stain. It turned out very well. The wood looked antique and we received lots of compliments. Disclaimer: I'm not expert, I just know what I like.

Adding to my original post - The first pics I included are of the House as it is now. It shows the reddish brownish creamish brick & shows how it looks in different light. The last pic is of the Estate Gray color roof we are having done. I will now post a pic of the cedar color we like for the stain on the replaced posts on the front porch, as well as the Sherwin Williams Mt. Etna color we were thinking of - but it might be too dark...

Your window panes appear to have divided lights. I'm not sure if you are thinking of hiring a painter, or doing the painting. Either way, the painter is going to charge to do all those divided lights, or you are going to be doing painstaking work yourself. White is very fashionable now, but once you paint woodwork white, it will never go back to being stained wood. To prep, you need to sand lightly every single surface, then primer to keep the color from bleeding, and then you will need to fill every little hole and crevice that you didn't know were there until you put white on it, and how they look bad. Then you can apply the paint. So, I'm thinking that the white has been around for about 20-25 years now. Fashion will be swinging back to the darker colors again, as it has already shown up in cabinetry. The woodwork will have to be replaced if you change your mind and want stained wood in a few years. I agree with the comments about using lighter colors in your furnishing and even artwork on the walls.