1. Observe and protect
Write down the symptoms, stop further damage if it's safe to do so, and gather whatever roof history is available.
2. Evaluate the house and site
Between mature tree canopy in DuPage's older subdivisions and the wind loads from events like the 2024 EF3 tornado and the 2020 derecho, a Naperville roof's fastening, flashing, and drainage usually tell you more than its age alone.
3. Define a written scope
Get preparation, protection, materials, permits, testing, cleanup, exclusions, and change-order terms spelled out in writing.
4. Compare providers
Compare the reasoning and boundaries behind each proposal, not just which total is lowest.
5. Inspect closeout
Confirm testing happened, the site is clean, documentation is handed over, and you know what maintenance is left to you.