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This is an interesting photo. I think that the way the roofline comes down in that fashion makes the roof look very much like an original. I'm thinking that perhaps you could have the roof come out at an angle from the vantage point of where you are seeing the exterior elevation of the stairs and the back porch area???
This capped structure looks nice brings back a cottagey feel to that area of the house. I also like the upper windows being so symmetrical, not a fan of the long rectangular window though. Perhaps you can create another swoop in the roof to somehow make the addition more cohesive with the original roofline.
Mike, I think this photo is very much reminiscent of what you are trying to accomplish with the swooped room and the entry room. I think that the cabin will look great with that and I can envision this with the solid wood arched doorway and a little less busy rafters and perhaps smaller corbels or supports. It also has dormers work very well with that swoop in the roof.
This has some interesting aspects that I think could be applied to particularly there stairwell area. I especially like how the dormer roofline connects to the side roofline and it actually goes lower and wraps around the shed dormer roofline.
Q