Asphalt shingles on the slant?
I am about to replace the shingles on a shed roof that slants two ways. Should the shingles go on at right angles to the direction rain will flow down the roof? Or can the shingles go on parallel to the gutter edge even though the flow line is about 20 degrees off?
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Sounds like the house that Jack built. Maybe Jack should answer this but I'll take a stab.
You don't mention the pitch or the climate and it is unclear whether this roof is on a leaning shed or a shed style roof with a designed roll on living space.
But as a wild gues at generalizing, I would feel comfortable either way if it is pitched at 6/12 or better. Less and ytou might need ice/watershield or follow the drip line.