John,
Did you see the article on timber framing in Nepal (or maybe your wrote it). I don't think I saw any hips while I was roaming around Nepal. I'm not sure what you mean by sill. Do you mean the top the masonry wall in this case? If so, you could run a top timber plate over the masonry.
What size building is this? Trusses are often used to support hips, but I wouldn't mess with hammerbeams unless you really really know what you're doing. Often hips sit on a tension ring of some kind. It would all depend on the size and snow loads and so on.
And to get the gutter track level on irregular roofs, just draw an elevation view with the 2 common pitches, and graphically or mathematically make them the same height.
And if you want the overhang to be the same dimension horizontally (the soffit)(in plan view), then you have to offset the hip off the corner of the building.