Check the license and insurance first, before you ever talk price
The license and insurance check is the foundation of the whole hire, and it takes about two minutes. In Oregon, every legitimate roofing contractor carries an active CCB (Construction Contractors Board) license, and you can look it up yourself on the CCB website. Hiring someone without one can void your permits, expose you to liability, and leave you with no real recourse if things go sideways.
Do not stop at the license number. Ask for actual insurance certificates for both general liability and workers' compensation. Then call the insurer using the phone number printed on the certificate, not a number the contractor hands you, and confirm the policy is active. That one phone call catches more problems than any other step in the process.
- Confirm the license is active, matches the contractor's legal business name, and is not expired
- Verify general liability coverage, which protects your property if something gets damaged during the job
- Confirm workers' comp coverage, which protects you if a worker gets hurt on your roof
- Check for complaints or disciplinary history through the CCB while you are on the site
Why three itemized bids, not one good feeling?
Three written estimates is the minimum because it is the only way to compare apples to apples. A lump-sum quote tells you almost nothing. It hides what materials are being used, whether permits are included, and what happens if the decking underneath turns out to be rotted. An itemized bid forces the contractor to commit to specifics, and those specifics protect you once the job starts.
Comparing three bids also helps you spot the outlier. A bid that comes in dramatically lower than the others is not a deal. It is a sign that something got left out of the scope, and you will meet that missing item later as a surprise charge.
- Labor costs broken out from material costs
- Material specifications with brand names and product lines, not just "shingles"
- Permit and inspection fees listed as their own line item
- Debris removal and disposal costs
- Underlayment, ice and water shield, flashing, and ventilation details
- What the decking inspection covers, and what happens if damage is found
What actually belongs in the contract?
A roofing contract should spell out the full scope of work, the exact materials with manufacturer names, start and completion dates, and the complete payment schedule. A vague contract is almost as bad as no contract, because verbal promises do not hold up when there is a dispute over what was agreed to.
Pay special attention to decking. It is common to find damage once the old roof comes off, and you want the price per sheet of replacement decking agreed to in writing before work starts, not negotiated on the fly while your house is open to the sky.
One more thing on money: never pay everything upfront. A reasonable deposit is somewhere in the 10 to 30 percent range, and the final payment should wait until you have done a walkthrough and confirmed the work matches the contract.
- Full scope of work, including layers being removed and decking inspection terms
- Timeline with start date, estimated completion, and weather delay provisions (this is Oregon, it will rain)
- Workmanship warranty terms and manufacturer warranty details tied to installer certification
- Payment schedule with deposit amount, progress payment triggers, and a final holdback
- Lien waivers, so a supplier cannot come after your house if the contractor skips a bill
- Cleanup expectations, daily and final
- A termination clause so both sides know how to exit if it goes wrong
Budget honestly and watch for the red flags
Roof costs vary a lot depending on size, pitch, and materials, which is exactly why itemized bids matter. A bid that looks cheap on the surface often excludes permits, disposal, or proper underlayment, and those omissions show up as surprise charges once the job is underway. Build permits and inspections into your budget from the start. A contractor who suggests skipping permits to save money is putting you at risk, not doing you a favor.
If the damage is storm related, put the contractor's scope and your insurance approval side by side before you sign anything. When those two documents do not line up, supplemental claims get denied and you end up holding the difference. Our storm damage and insurance guide walks through how that process works in Oregon.
- Bids with no line items or vague material descriptions
- Pressure to sign because "the price is only good today" (real prices survive a night's sleep)
- Requests for large upfront payments before materials are even ordered
- No mention of permits or inspections anywhere in the scope
The questions that show you who you're hiring
The questions you ask before signing tell you more than any website will. A contractor who answers clearly and without hesitation is showing you how they will run your job. One who gets vague or defensive about licensing or permits is showing you that too. If you want the full list, start with our roofing 101 guide, and make sure you cover these at a minimum.
- "Can you provide your CCB number and current insurance certificates?"
- "Will you pull the permit and coordinate the inspection?" Anyone who says a full replacement does not need a permit is wrong.
- "Are you a certified installer for the shingles you're proposing?" Manufacturer warranties usually require certified installation, so this affects whether your warranty is even valid.
- "Can you give me three recent references nearby?" Then actually call them.
- "Will your own crew do the work, or will you subcontract it?" It affects accountability and warranty coverage.
- "How do you handle changes to scope or unexpected costs?" The only good answer is: in writing, with your approval, before proceeding.
What I've learned after a decade on Portland metro roofs
I have been doing this since 2014, and the homeowners with the worst stories almost always skipped one of the basics. They hired someone without checking the license, or signed a one-page contract because the contractor seemed trustworthy. I get it. Roofing is stressful, and when someone shows up confident and friendly, it is easy to relax your guard. My rule: trust your gut on personality, verify everything on paper.
The other thing I see constantly is people caving to pressure. Someone says the price is only good for 24 hours and they sign without comparing bids. That is not how legitimate contractors operate. A real professional gives you time to review, because they know their work and their price hold up to comparison.
The best hire I have ever watched a homeowner make was someone who showed up with three other bids, a list of questions, and a clear idea of what belonged in the contract. That project went smoothly because both sides knew exactly what to expect. That is the standard to aim for, and honestly, we like customers who do their homework. It means we are being compared on the things that matter.