Are you wanting to just update the look or needing to do something to the roof because of the snow? For a mountain house I always think stone looks nice and think it would look nice on the bottom part of this house. Is the brown building to the right a garage? If so maybe should play off the garage color and trim the house with the same brown color. Do you want to keep the current color on the house? If you like blue or green colors, I think an green house color at the top would be nice but you would need to pick out the right green color. I found a sample of a green craftsman house for you.
http://www.lurvely.com/photo/3662267214/And_now_in_craftsman_colors/
Good luck.

HI -- It is kind of a blank canvas,isn't it ? . How about going more with some Art Deco style with the formed trims , and then the whole building could have a stucco finish , This would be the easiest way to go ,other than going totally modern ,easier still . I don't see any possible Craftsman style here at all. You must have to shovel the roof if there is a lot of snow . Someday when you need a new roof ,maybe think about adding a peeked or shed slanted roof , probably a metal one would be the best. I don't know how or have a program to show how it would look , sorry . Some of the other Houzzers can do this , but see if an architect can draw it out for you depending on what their fees would be .You can get an idea if you look up Art Deco and Modern house exteriors on this site , that should help .

In the Canadian Rockies (read: 2-4 meters of snow per year) the only roof worth looking at is metal with a steep pitch. That being said, there must be some form of protection for the entrance against the snow sliding down.

I'm not sure how much snow is "lots of snow", but this is the only form that is "happy-happy" in the Rockies. You can go with slate looking or tile-looking but still...metal roof with steep slope. The Europeans have hundreds of looks for metal roofs! Red, blue, green, shingles, slate, tile! These roofs can go 50 years. The down side, the initial investment.

Hi again. . "Blank Canvas in the extreme!" It's in N. Idaho. The roof behind the parapet is sloping toward the back. I already popped IN the new entry to break up the front. The old entry w the crappy gable was since abandoned. I can do any or all the work. Not settled in any way on colors either. Like the idea of stone or sim to ground the building. Also I have opportunity to add a longish deck on the left in order to put a carport there, or possibly another garage door element. Crummy photos I know.

To get a good look at different paint colors, go to the Sherwin Williams website. You can upload a photo of your house.

For changes, I suggest putting a new portico or small metal roof over the new front door, remove the old entranceway completely, and replace whatever windows don't match. Add lighting by the front door. Patch the siding where bits and pieces are missing. Then paint with three colors: a main color and two trim colors. The windows look new, so use that color white as one of your two trim colors. Pruning back the trees before they leaf out in spring will help enormously on back and sides. Gutter cleaning is boring but essential. Pruning the trees back will help keep leaves out of the gutters.

Thanks for all the input. Gonna try to implement some elements ASAP.! Hopefully get a look at some options on paper somehow.