How Many Quotes Should I Get on My Roof Replacement?

If you've searched online for the answer to this question, you've probably read the same advice over and over:

"Always get three quotes."

It's not bad advice. But after years of inspecting roofs, writing estimates, and sitting across from homeowners making one of the biggest investments they'll ever make, I've come to a different conclusion.

You might only need one quote.

You might need five.

The right number isn't determined by a rule. It's determined by when you find the contractor you trust.

Because here's the truth:

Study the person, not the quote.

The quote matters. The price matters. The materials matter. But none of those things matter as much as the person who will ultimately decide how your roof is installed.

That person will make hundreds of decisions you'll never see.

Will they replace the flashing correctly?

Will they install the proper ventilation?

Will they stop and fix an issue they discover halfway through the project?

Or will they take the shortcut because nobody will ever know?

Those decisions aren't listed on a price sheet.

They're determined by the character and experience of the person doing the work.

The Biggest Mistake Homeowners Make (in my opinion)

The biggest mistake I see homeowners make is collecting three quotes and letting price become the deciding factor.

Many homeowners assume that if every contractor is replacing the roof, then every proposal must include the same work.

Unfortunately, that's rarely the case.

Price begins to replace trust.

Instead of asking, "Who do I want protecting my home?" homeowners begin asking, "Who's the cheapest?"

Those are two very different questions.

A Roof That Was Only 2 Years Old

One inspection has stayed with me for a long time.

We happened to be working nearby and offered to remove some brush that had collected on a homeowner's roof.

The roof was only about two years old.

As soon as I got on the roof, something didn't look right.

There was no wall flashing where there should have been.

Then another thought immediately crossed my mind.

"If the flashing is missing, I wonder if the drip edge is too."

Sure enough, there wasn't any.

The fascia boards had already begun deteriorating because water had nowhere to drain properly.

The homeowner had no idea.

Why would they?

Most homeowners don't know what drip edge is supposed to look like, let alone realize it's missing.

When we reviewed the original proposal, everything suddenly made sense.

Drip edge wasn't included.

Neither was the flashing.

Technically, the contractor installed exactly what they proposed.

The homeowner had chosen the lowest quote because it fit the budget.

Ironically, the difference between that proposal and ours would have covered the missing drip edge and flashing.

The lesson wasn't that the contractor was dishonest.

The lesson was that the homeowner thought they were comparing identical roofs when they weren't.

Two Quotes Can Use the Same Shingles and Build Two Completely Different Roofs

This is something many homeowners never hear.

A proposal can look nearly identical on the surface while being very different underneath.

One contractor might include:

• New drip edge

• Proper step flashing

• New pipe boots

• Manufacturer-required starter shingles

• Synthetic underlayment

• Proper ice and water protection

• Ventilation improvements

• Complete cleanup and final inspection

Another proposal might quietly omit several of those items.

Sometimes it's hidden in small print.

Sometimes it simply isn't listed.

I've seen proposals that mention "Drip Edge Extra" in tiny print that most homeowners would never notice.

I've also seen contractors:

• Reuse old flashing

• Leave out drip edge entirely

• Install fewer rows of ice and water protection

• Flip regular shingles upside down instead of installing proper starter shingles

• Skip ventilation upgrades

• Reuse aging pipe boots

Every one of those shortcuts saves time or money.

Every one of those shortcuts shifts the risk to the homeowner.

That's why comparing prices without comparing scope can be incredibly misleading.

The Contractor Who Earned the Job

Not every story is about someone choosing the lowest price.

Recently, I inspected a small metal roofing project for a business owner.

While I was there, we looked over the existing asphalt roof.

Everything about it looked right.

The flashing.

The drip edge.

The overhang.

The ventilation.

The details were all there.

Curious, I asked why he chose that contractor.

His answer was simple.

"I asked them what they'd do on my roof that the next guy wouldn't."

The contractor didn't give a generic sales pitch.

They explained their process.

They explained why they did things a certain way.

They answered questions confidently.

They earned trust.

They weren't the cheapest quote.

But they built a roof that reflected their experience.

Sometimes a few honest answers tell you far more than a few hundred dollars ever could.

Five Questions Every Homeowner Should Ask…

After hundreds of conversations with homeowners, these are the five questions I believe separate experienced professionals from people who are simply selling roofs.

5. How long have you been doing this?

Experience matters.

Roofing isn't learned overnight.

Someone who's spent years solving problems has likely seen thousands of situations they'll recognize immediately.

That experience often prevents costly mistakes before they happen. Everyone has to start somewhere but with a trainer.

4. What are you doing about my ventilation?

A generic answer is:

"We'll replace the existing vents."

A better answer explains the relationship between intake and exhaust ventilation. Did the roofer even check your intake vents?

A knowledgeable contractor should evaluate whether your attic is properly balanced, whether ridge ventilation makes sense, and whether additional soffit ventilation would improve airflow. Not just tear off and replace your shingles.

Proper ventilation helps extend the life of your roof and can improve attic performance.

3. How long will my project take?

If someone guarantees every roof will take exactly one day, I'd ask more questions.

Weather changes.

Hidden damage happens.

Unexpected repairs arise.

An honest contractor is comfortable saying your roof should take 1-2 days or 2-3 days if your roof is larger and more complex.

Sometimes realistic expectations are a sign of professionalism.

2. What happens after the roof is finished?

A good contractor doesn't disappear after the last nail is installed.

They return.

They perform a final walkthrough.

They answer questions.

They make sure the property is clean.

They pick up anything that may have been missed.

Finishing the roof isn't the end of the project.

Making sure the homeowner is completely satisfied should be the ending.

1. What will you do on my roof that the next roofer might not?

This question reveals almost everything.

An experienced contractor should immediately begin talking about details. No thinking required.

Maybe they'll discuss documentation.

Maybe they'll explain flashing.

Maybe they'll mention ventilation.

Maybe they'll explain how they prevent common installation mistakes.

Whatever their answer, it should reassure you that they've actually thought about what separates their work from everyone else's.

Communication matters.

A contractor who communicates well before the project usually communicates well during it too.

When Price Becomes the Focus

I've sat at countless kitchen tables where I could tell a homeowner understood the value being presented.

Then I'd follow up a few days later.

Something had changed.

it wasn't trust.

It was price.

I understand that completely.

Replacing a roof is expensive.

Most people don't wake up hoping to spend thousands of dollars on shingles.

But I've often wondered how many homeowners would have found a solution if they'd simply told their contractor:

"This is honestly more than I can afford."

A good contractor shouldn't immediately walk away.

Maybe financing makes sense.

Maybe insurance should be explored.

Maybe the project scope can be adjusted responsibly.

Maybe there's another option.

As I often tell homeowners:

We don't have problems. We have solutions.

What I Would Tell My Own Daughter (Willow)

If my daughter called me one day and asked how many roofing quotes she should get, my answer would be simple.

Get as many as you need.

But stop the moment you find the person you trust.

Study the person.

Not the quote.

Find the contractor who makes you feel confident they won't take shortcuts when nobody is watching.

Once you've found that person, have an honest conversation.

If the proposal is outside your budget, say so.

Talk about financing.

Ask about insurance.

Discuss options.

The right contractor won't treat you like another sale.

They'll work with you to find the best path forward.

Even if compromises have to be made, you're making those decisions with someone you've learned to trust.

That's worth far more than choosing the lowest number on a sheet of paper.

So...How Many Quotes Should You Get?

Here's my answer.

Get one.

Get three.

Get five.

Keep collecting quotes until you meet someone you genuinely trust with your home.

Because you're not buying shingles.

You're not buying nails.

You're not buying underlayment.

You're buying the judgment, experience, integrity, and communication of the person who will make hundreds of decisions you'll never even see.

Those decisions determine whether your roof protects your home for decades or becomes a source of frustration a few years later.

If there's one thing I hope you remember long after reading this article, it's this:

Focus on trust. Focus on the person. Then worry about the price.