Project Sequence Roof-Siding-Paint

It is getting close to replacing the roof and the cedar shingle siding on our home. I figure it is a good time to repaint the exterior trim too.
Which brings up the question:
What's the appropriate sequence to make sure everything gets properly flashed during the job and to get the best paint job?
The house is two story, with an asphalt shingle roof. The attached garage is one story story, so where it joins the rest of the house, there is a transition from the cedar shingle siding to the asphalt shingle roof.
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roof-siding-then paint

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Remove lower portion of siding where wall meets garage roof.
Roof with proper step flashings.
Siding with underlying flashings.
Caulk and paint.
Colbyt
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