Roofing Done Right: There’s No Such Thing as Asking Too Many Questions
Author: Zak Hutsul
Date: Mar 07, 2025
4 min read
The roof over your head has served you well for many years, but now it’s showing early signs of aging.
There are dozens of roofing contractors to choose from, but how do you know how to choose the right one for you?
The short answer is, it’s an educated guess.
I hope the following information proves to be just as useful to you, as it was for me, when I was helping my dad hire a roofing contractor this past summer.
The Warranty Up-Sell: What You Need to Know
A "lifetime warranty" might sound reassuring, but here’s the thing—it’s mostly a sales tactic.
Contractors go in and out of business all the time, and once they close shop, your warranty goes with them.
A standard workmanship warranty typically lasts two to three years, while manufacturer warranties on shingles specify a 25-year period.
Always ask your roofing contractor for specifics, get everything in writing and work with contractors who can show you jobs done 2, 5, or even 10 years ago.
Shingle Grades: Choosing the Right One
Not all shingle grades are created equal.
Architectural and designer grade shingles provide almost the same protection against the elements. Designer grade shingles have the upper hand when it comes to curb appeal and aesthetic value for homes that command a luxury roofing material.
Both grades are known for durability and long-term performance.
Beyond the brand or the grade of shingles, make sure to ask for a full report and pictures of the underlying wood decking. If any decking needs replacing, insist on plywood and clarify the cost per sheet (expect around $90 per sheet).
Ice, Water, and Underlayment: An essential factor not to be overlooked
Your roof isn’t just about what you can see. What you don’t see is what matters the most. A proper installation should include:
At least three feet of ice and water shield (like CertainTeed Grace Vycor) along eaves, valleys, and around vents and flashings.
A complete synthetic underlayment system nailed down, securely, not just stapled in place temporarily.
The Right Questions Make All the Difference
Before signing a contract, run through this checklist with your roofer:
Do any flashings or vents need replacing?
Will metal flashings be caulked to brick/wall surfaces?
Will the eaves be cleaned after installation?
What kind of site protection and cleanup do you include? (This should cover bin disposal and magnetic nail pickup.)
How many nails per shingle? (Four is standard, six is better.)
Who's Actually Installing Your Roof?
Not all roofing companies operate the same way. Some are owner-operated, while others have a more corporate structure with in-house staff and subcontractors.
Ask:
Who will be working on your home? (Get names if possible.)
How long have these employees been with the company?
Can they provide references from jobs completed 5+ years ago? (This tells you how well their roofs hold up over time.)
Do they have liability insurance? (Always ask for a copy.)
Are they properly licensed? (Requirements vary by region.)
Cost Expectations: What’s the Bottom Line?
Ballpark pricing for a 2,500 sq. ft. roof:
$8,000 - $9,000 (varies based on pitch, materials, and add-ons)
Around 65 bundles of shingles used per 2,500 sq. ft.
Always get a detailed, itemized quote that aligns with the Ontario Building Code. If something feels vague or rushed, don’t hesitate to ask for clarity.