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The only other way I see, would be to extend the addition roof plane, & also the existing big roof plane so that there would be two big planes with a common ridge. That ridge would be higher than any of the existing roof. From the front view, you would have a small hip (kinda like a Dutch hip) sticking above the main ridge. It would be way more expensive, but would be simple shingle system.

Scipio's method should work fine, but as mentioned, I'd raise the slope, do a membrane, & then shingle main last. The hard part would be getting the membrane up under the existing roof. If your redoing the adjacent shingles, it's not a problem.

Joe
 
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