I'll suggest complementing nature rather than trying to blend in. Shingles same as the siding -- change in texture, not color. I don't see traditional-transitional here, rather an attempt to craftsmanize a house that lacks any resemblance to craftsman. I noticed you have not started an ideabook, so no way of knowing your style. Is your builder/designer/architect unable to do color renderings like I showed above?

The thing I noticed about snow when I drove by houses, is that white trim or garage doors will not match. The whites really clashed. I went with colonial white and cannot believe what a perfect beautiful creamy white it is. I expected it to be more crisp and stark and its not. However its not yellow either. Happy to say after struggling between snow and colonial that I am very happy I choose colonial. Hope that helps.

If your house is well insulated, the darker siding shouldn't affect internal temperature, as nsc6 said. The only way you can assure you won't tire of the house is to use something like HardiPlank that you can paint in 7 to 10 years if you tire of the color. It's quite a bit more expensive than vinyl though. Will you be living here full time or is this a vacation home? If it's a vacation home that you won't be driving up to every day, I think it would be a nice change to have something a bit different than you see driving down your street to your home every day. If it's a weekend and vacation getaway, it should feel special. Honestly, it should feel special even if it's going to be your everyday home. You could leave the brown window trim. It would work well with the cedar siding.

We had a hailstorm last year and had to have our roof replaced. Where we live several houses were having their roofs replaced and our HOA calls for you to have the color “weathered wood”. We started noticing lots of roofs being replaced and the newer shingles are very speckled looking! a house that has a lot of variation in the brick can really look a little crazy if the roof is speckled also. I would just be really careful picking what looks like architectural shingles using sample pictures. If you call the roofing supplier or your roofer they should be able to give you addresses of the colors of shingles you’re interested in so you could actually drive to by that home and see the shingles on an actual home. We found it very helpful and the color “weather wood” is very different looking across different brands of roofing. We chose Malarkey brand their Legacy line in “Weathered Wood” color upgrading to the class 4 impact resistant shingles. you also might check with your insurance company because we paid a little extra to get the class 4 impact resistant shingle and we get a discount on our insurance. Just a few things I learned while picking Roofing last year!