Why the plan reads short. A roof plan is a view from above, so a sloped plane appears at its horizontal footprint. The real surface is the footprint times the slope factor, the square root of one plus the rise over run squared. At 6/12 that factor is about 1.118, and at 12/12 it is about 1.414, so the steeper the roof, the further the drawn area falls short.
One pitch, many planes. When every plane of a roof has the same pitch, as on a simple hip or gable roof, the factor applies to the whole footprint at once. One outline along the eaves gives the full sloped area, and there is no need to trace each hip triangle. Sections at different pitches, such as a porch, a shed dormer, or a low-slope area, need their own outlines and their own labels.
How MeasureSet reads a pitch. Select an area and type the slope in the Roof slope box. It accepts rise over run as 6/12, 6:12, 6 in 12, or a bare 6 meaning six in twelve, and also degrees such as 30° and percent such as 50%. The steepest slope it takes is 24/12. With metric units, a bare number reads as degrees. In the spreadsheet export a slope is written as 6 in 12, so Excel does not mistake it for a date.
Lines on a roof. The slope factor applies to areas only. Eaves and ridges are level, so their plan lengths from the length tool are their real lengths. Rakes, hips, and valleys climb with the roof, so they read short in plan; MeasureSet does not lengthen them, and those figures need adjusting in your spreadsheet.
Waste and squares. Type a waste percent on a label and every area with that label carries it; the totals then show sloped area and the figure with waste. A roofing square is 100 square feet. MeasureSet reports square feet, square meters, or square yards, so dividing into squares and bundles is a spreadsheet step, along with any pricing, since there are no assemblies or cost database.
Drawings, not aerial images. MeasureSet measures roof plans in a PDF drawing set. It opens PDF files only and does not measure an existing roof from photos or satellite images, so a reroof with no drawings is a different job. When drawings exist, calibrate the roof plan sheet from a printed overall dimension, check one more with the segment tool, and remember that a measurement is only as good as the calibration and the drawing it comes from.