Do I need to re-enter dimensions for each trade?
Not the building itself. Length, width, wall height, and openings are entered once and propagate into Room Layout, Framing, Roof, and Siding, and on into Shingles and Sheathing through the roof area. Two things stay their own entries because the footprint does not determine them: the footing diameter, depth, and post count that drive Concrete, and the roof run. If the run disagrees with the building width for the roof type you picked, the calculator flags the mismatch rather than silently overruling the number you entered.