Phase Two of Roofing Project Begins

I will have someone here to answer the construction questions when the time comes. But before I go tearing out the old roof, I thought it pertinent to air a few questions here.
The following picture shows the approximate roofine for the new roof. I'm wanting to cut into the siding to remove the bottom portion, which will allow a snug fit against the sheathing, plus a way to seal the seam with flashing. Seems like the easiest way would be to chalk a line and just cut in place. Does anyone see any problem(s) with that plan? Thought it would be easier to do this with the old roof still there.
http://www.peacefulbendvineyard.com/test/roofline.jpg
A little background, this is a roof that covers a 10 ft deep cellar. It is about to be razed and then raised to 14 ft (from floor level) on the low end, and 18 ft 2 in on the high end, with the center area being completely open.
Second to last picture on the following page shows the opposite side (from the previous picture) as it joins the other, barn shaped building. This poses a little extra challenge with the compound angle:
http://www.peacefulbendvineyard.com/test/roof2.shtml
Here's the initial basic plan:
http://www.peacefulbendvineyard.com/test/plans.jpg
I'm vasilating on whether the opposite "support wall" is necessary.
TIA for any assistance,
clyde
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wrote:

No comments on your support question, just an observation that your structure looks like a perfect candidate for sheet metal roofing if you can afford it. Good luck!
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Yep, we looked long and hard at metal roofing. For the time being, the price was the most impactive factor. As is more than obvious, this project is long over due and until this bird of a business is flying a little higher, we need to squeeze every penny. I've concluded that eventually we will cover everything in metal, but I'm bent on doing it in standing seam, which means it needs to be pre-ordered. With all the changes in the roof diminsions, this would be rather tricky if not impossible. I figure that I can get it on well enough to last a decade or so, then we'll place an order for the good sheets and get it done right.
clyde
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