On the historic stock, steep pitches shed water well but the problems are structural and detail-driven. Original decking is often plank with wide gaps. Flashing at chimneys, dormers and complicated wall intersections is frequently the weakest element in the assembly, and much of it has been patched repeatedly over decades. Hail on steep slopes strikes at a glancing angle, so the classic circular bruise pattern is less pronounced and the damage often concentrates on the low-slope porch roofs, dormer cheeks and horizontal surfaces instead.
On the newer west-side subdivisions the story is conventional: architectural asphalt on moderate pitches, first-generation roofs now entering the age where seal strips weaken, and open siting on former farmland that gives wind a clean run. Those roofs are simpler to inspect and simpler to scope, and the failures show up in the field and at the ridge rather than at ornate flashing details.
Kane County sits in the same convective corridor as its neighbors to the east, and homeowners can confirm specific event dates using National Weather Service Chicago event summaries rather than relying on a contractor's word for when a storm occurred.