What My Mom Wishes She Knew Before Hiring a Roofer | GetAHomePro
What My Mom Wishes She Knew Before Hiring a Roofer
·12 min read
D
David MartinezCertified Roofing Contractor
Published March 20, 2026
Key Takeaway
My mom hired a roofer alone after Dad died and ended up paying $23,500 for a job that should have cost $16K. Here's what she wishes she knew.
I almost didn't write this.
My mom would be embarrassed. She'd say, "Why do you have to tell everyone our business?" in that way she has — half scolding, half laughing, one hand already waving me off.
But I keep thinking about that bucket.
The plastic blue bucket she put in the corner of the spare bedroom. The one with the dark stain ring on the carpet underneath it. The one she'd been emptying for three weeks before I showed up for Sunday dinner and saw it sitting there, quiet and patient, collecting drips from the ceiling above my dad's old armchair.
She didn't tell me. She didn't want to worry me.
That's the part I can't shake.
Her House. Her Problem to Fix.
My mom's name is Rita Santos. She's 72, early 70s, Portuguese-Canadian. Born in the Azores, came to Canada in her twenties, spent forty years building a life with my father Manuel in a house they literally built together on Keele Street in Vaughan, just north of the old Woodbridge neighbourhood — back when that stretch was still farmland and the nearest grocery store was a twenty-minute drive.
My dad passed six years ago. Pancreatic cancer. Fast and terrible, the way it always is.
The house is all she has left of him. The kitchen where he made bacalhau on Fridays. The garden he tended every summer until he couldn't. The chimney he was so proud of — "Portuguese stone, not that Canadian drywall," he used to say, not really knowing what he meant but meaning it completely.
My mom has lived there alone since. She maintains it. She shovels. She calls the furnace guy. She knows which circuit breaker controls the kitchen and which one controls the garage. She is not helpless. Not even close.
So when the roof started leaking last February — after one of the worst winters the 400 corridor has seen in years, freeze-thaw cycles stacking up week after week — she didn't call me.
She handled it.
The Flyer in the Mailbox
The leak showed up near the chimney. A slow drip at first, water staining the ceiling of the upstairs hallway just outside the spare bedroom. She put down a towel. Watched it.
GAF Master Elite Certified, HAAG Certified Inspector, 15+ years experience
David Martinez is a GAF Master Elite Certified roofing contractor and HAAG Certified Roof Inspector with 15 years in the roofing industry. He has overseen more than 2,000 roof replacements and repairs, specializing in asphalt shingle, metal, and flat roofing systems.
Want a real quote, not an estimate?
Text us what you need done. We’ll connect you with a contractor who’ll call you with an actual number.
By late March it was worse. She knew she needed a roofer.
She didn't Google it. She doesn't really Google things. She found the flyer.
Steve's Roofing. A photocopied half-sheet that came in the mailbox sometime in early April, wedged between a Domino's menu and a Shoppers Drug Mart flyer. Local company. Vaughan area. "20 years experience. Seniors discount. Free estimates."
She called the number.
Steve came the next day. Drove a clean white truck. Called her "Mrs. Santos" from the moment he got out of the driveway. Complimented the house. Asked about the chimney — "Beautiful stonework, Mrs. Santos, they don't build them like this anymore."
He also brought his wife.
This detail matters. His wife spoke Portuguese. Not fluently — she was Romanian, had picked it up from customers over the years, she said — but enough. Enough to make my mom feel comfortable in a way that she doesn't always feel when strangers come to the house. Enough to make her trust.
That trust is worth something. I understand why it happened. I'm not blaming my mother for a single second.
I'm telling you how it works because maybe it'll work on someone you love too.
The Quote. The Handshake. The Half-Down.
Steve walked the roof. He was up there for maybe twenty minutes. Came down with a yellow legal pad and a number.
$14,000.
Partial re-roof around the chimney and the front slope. New shingles, new underlayment, he'd "take care of the chimney area," make sure everything was sealed properly. He could start in two weeks.
My mom thought about it overnight. She called her neighbour Maria, who said it sounded reasonable. She didn't call me. She didn't call my sister. She signed Steve's one-page contract — which was really just a price sheet with a signature line — and wrote him a cheque for $7,000.
Half upfront. Half on completion.
She told me about this part later in a way that made me understand she knew, even then, that it might not be right. But she didn't want to ask me because she didn't want me to take over.
Steve's crew arrived on a Tuesday morning in late April. Three guys. Done in two days. From the ground, looking up, it looked fine. New shingles, clean lines. Steve walked her through it, pointed out the work, collected the remaining $7,000.
She was proud. She'd handled it.
The First Rain
The first real rain came the second week of May. Heavy overnight stuff, the kind that drums on the windows.
The leak was back.
Same spot. Same ceiling stain, now darker, now spreading. She called Steve. He came back within a few days, went up on the roof, came down and said he'd patched a couple of spots that hadn't sealed properly. "It happens sometimes with the first rain, Mrs. Santos. You're all set now."
She believed him.
The Bucket
The second rain was worse.
Water came through the hallway ceiling again — and now through the ceiling of the spare bedroom too. The room with my dad's old reading chair. The room where we still keep his books on the shelves the way he left them.
My mom got the blue bucket from the basement. Placed it under the worst drip. Told herself she'd call Steve in the morning.
She called. Left a message. He texted back two days later: "I'll get back to you next week, we're pretty slammed."
She waited.
She kept emptying the bucket.
She didn't call me.
Three weeks passed.
Sunday Dinner
I came for dinner on a Sunday in early June. Pasta e fagioli, the way she's made it since before I can remember. We ate. We talked about nothing much. I went to use the bathroom and walked past the spare bedroom and the door was mostly closed but not all the way and I saw it.
The bucket. The stain on the carpet. The water line on the ceiling.
I stood in that doorway for a long moment before I could say anything.
"Mom. Why didn't you call me?"
She was already in the kitchen, clearing dishes. She didn't answer right away.
"It's fine. I was handling it."
"There's a bucket in the spare room."
"I know there's a bucket."
"For how long?"
Long pause.
"A few weeks."
I didn't yell. I wanted to. Instead I sat down at the kitchen table and we had the conversation that I think both of us had been avoiding for six years — about the house, about what she can do alone and what she needs help with, about how asking for help isn't the same as giving up.
She cried a little. So did I. We didn't make a big deal of it.
Then we called an inspector.
What the Inspector Found
The inspector's name was David. He came two days later, spent two hours on the roof and in the attic. His report was 14 pages.
The short version: the flashing around the chimney had never been properly replaced.
Steve's crew had installed new shingles over the old flashing — original 1986 flashing, the same age as the house. The counterflashing, the piece that seals where the chimney meets the roof, was still the original. Forty-year-old metal, cracked, corroded, never touched.
New shingles over bad flashing doesn't fix a leak. It just covers it up until the next rain.
Any licensed roofer knows this. It's not an edge case. It's roofing 101.
When I called Steve, he had an explanation ready.
"The flashing wasn't part of the quote."
I asked my mom what he'd said when he walked the roof back in April.
She said he specifically told her he'd "take care of the chimney area."
Nothing in writing. No scope document. No line items specifying what "take care of" meant. Just a one-page price sheet and a handshake.
Steve stopped returning calls after the third one.
The Real Number
We hired a proper roofing company — licensed, insured, referenced, WCB-verified — to do what Steve should have done.
They replaced the flashing. All of it. Counterflashing, step flashing, the works. Reflashed the entire chimney, resealed the front slope, fixed the water damage to the sheathing underneath.
$9,500.
Add that to the $14,000 already paid to Steve.
$23,500 total. For a job that a good roofer would have done properly for $16,000 to $18,000 the first time.
My mom paid $5,500 to $7,500 extra because a guy with a flyer and a charming wife told her he'd "take care of it."
What I Understand Now
For a long time I was angry at Steve. I'm still not thrilled with him.
But the part that really stays with me isn't Steve. It's the bucket.
The bucket she hid for three weeks because she didn't want to be the widow who couldn't handle her own house.
My mom is not naive. She's not fragile. She raised three kids, ran a household, learned English in her forties, buried her husband, and kept going. She is one of the toughest people I know.
She didn't hire Steve because she was foolish. She hired him because he showed up fast, was kind to her, and his wife spoke a few words of Portuguese. She paid him because the number sounded reasonable and she wanted to prove she could still do this on her own.
She hid the bucket because she was afraid that needing help meant losing something — some piece of herself that she'd been holding onto since my dad died.
She wasn't being stubborn. She was trying to prove she could still do this.
I get it now. I really do. I just wish I'd known sooner.
How to Protect Yourself (or Someone You Love)
If your mom, your dad, your grandparent, or anyone you care about is dealing with a contractor, here's what we learned the hard way.
1. Get the scope in writing — every line item.
"Taking care of the chimney area" means nothing legally and nothing practically. A real scope document lists exactly what will be replaced, what will be left, and what the job includes. If a contractor won't write it down, walk away.
2. Never pay more than 10-15% upfront.
In Ontario, a 50% deposit on a $14,000 job is a red flag. Established contractors have supplier accounts and don't need half your money before they've touched your roof.
3. Hire an independent inspector before and after.
A pre-job inspection tells you what actually needs to be fixed. A post-job inspection confirms the work was done right. David's two-hour inspection cost $350. That $350 would have saved my mom $9,500.
4. Check WSIB and liability insurance yourself.
Don't take a contractor's word for it. Ask for the certificate numbers and verify directly.
5. Flyer companies are not vetted.
A flyer in a mailbox means someone paid to print flyers. That's it. It says nothing about licensing, insurance, or quality.
6. If something feels wrong after the work — call immediately.
My mom waited weeks. The longer you wait, the harder it is to hold anyone accountable. Text, email, photograph. Create a paper trail from day one.
If you're in this situation — or you want to make sure someone you love doesn't end up in it — GetAHomePro connects homeowners with verified, insured contractors. Every pro is credential-checked before they appear on the platform.
Questions Readers Asked After This Story
Could your family sue Steve?
We talked to a lawyer. Without a detailed scope document, proving what Steve was supposed to do versus what he actually did is difficult. His one-page price sheet just says "partial re-roof" and a dollar amount. No mention of flashing. Our lawyer said we'd likely spend $3,000-$5,000 in legal fees to recover maybe $5,000. We haven't decided yet.
Does your mom still live in the house?
Yes. She's not leaving. The roof is fixed properly now. We've set up a system where she calls me or my sister before hiring anyone — not because she has to, but because we asked and she agreed.
How do I check if a roofing contractor is legit in Ontario?
Roofing in Ontario doesn't require a specific provincial licence (unlike electrical or plumbing), but legitimate contractors carry WSIB coverage and general liability insurance. Ask for certificate numbers and verify them directly. Also check Google reviews, HomeStars, and BBB. A flyer is not a credential.
What if my parent is too proud to ask for help?
This is the hardest one. My mom wasn't being difficult — she was being independent. The best thing I've found is to make it about being a team, not about taking over. "Let me help you check the quotes" is different from "Let me handle this."
My mom made pasta e fagioli again last Sunday. I went early. Before we ate, I walked upstairs and checked the spare bedroom ceiling.
It was dry.
The bucket is gone. My dad's chair is back in its spot by the window.
She caught me looking and said, "It's fine." But this time she was smiling.