Map every roof plane
Note pitch, material, valleys, dormers, chimneys, walls, skylights, plumbing vents, any flat sections, gutters, and drainage paths.
Look from the attic
Where it's safe to access, attic staining, frost, airflow, insulation gaps, and deck condition tell you things the exterior can't.
Plan for winter
Eaves, shaded valleys, insulation, ventilation, and safe drainage all matter through a season of repeated freeze and thaw.
Compare scopes, not totals
Ask specifically what happens at the deck, eaves, valleys, walls, chimneys, penetrations, ridge, and gutters, and what cleanup includes.