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Gable Flashing - Pergola to house

Hi, I need a flashing installed between a recently built gable pergola. The left side of the pergola is straight forward, with it possible to flashing under the rooffline or barge board. The right had is more difficult as the gable slopes against the weather board line. Options include stepping down the weather boards (preferred), cutting in to the weather board, and using silicon. Please see the photos and let me know..