A homeowner in Chicago called me two summers ago. She’d had her roof replaced the previous year. The contractor was the lowest of three bids, by about $4,000. She wanted to know who to blame because the roof was already leaking.
I had no involvement in the job. But I’d seen that story enough times to know how it ended before she finished telling it.
TL;DR: The cheapest estimate is rarely the best value. Homeowners who choose contractors based on price alone end up paying more in callbacks, repairs, and frustration. Learn what a good estimate actually includes and how to compare them properly.
The cheapest bid is usually the most expensive one
Low bidders leave things out. That’s how they get low. It might be the underlayment. It might be the flashing or the drip edge. It might be the permit, which means no inspection, which means you have no legal protection when something fails. But something is always missing, and you find out what it was when you’re already living inside the problem.
A $12,000 roof that needs $3,000 in repairs after two years wasn’t a $12,000 roof. It was a $15,000 roof installed by someone who wasn’t honest with you about the scope.
What a real estimate looks like
Materials and labor, broken out separately. Products listed by brand and model number, not just “shingles” or “composite decking.” A timeline. A clear list of what’s included and, just as important, what’s not.
If your estimate is one number on a page, that’s not an estimate. It’s a guess. You’re agreeing to pay someone based on a guess.
Ask for the warranty details in writing before you sign anything. Not the phrase “we guarantee our work.” What exactly is covered? How long? What’s the process if something fails in year two? A contractor who can’t answer that clearly has probably never had to honor it.
Three bids is the minimum
Get three estimates on anything over $5,000. Not because the middle number is right, but because three bids show you the range. If two companies land around $14,000 and one comes in at $8,000, that $8,000 number should make you nervous, not excited.
When you compare them, compare scope. Are all three bidding the same work? If one includes tear-off and the others don’t, you’re not looking at the same job. The only honest comparison is line item by line item.
Red flags in a contractor estimate
They want full payment upfront. No serious contractor needs 100% before they start. Standard is 10 to 30% down with the balance on completion. Full payment upfront means they have no incentive to finish to your standard.
They pressure you with a limited-time offer. If the price is only good today, it was never a real price. It was a sales tactic, and it tells you something about how they operate.
They can’t hand you insurance documentation on the spot. General liability and workers’ comp certificates should be ready when you ask, not “in a couple days.” If they need time to track those down, assume they don’t have current coverage, because that’s usually the reason.
They resist putting it in writing. There’s no version of this situation where a handshake deal protects you. If they won’t write it down, walk away.
The question most homeowners skip
Ask the contractor what could go wrong.
Seriously. “What are the risks on this project?” A contractor who’s done this for a few years will tell you about the possibility of hidden water damage, unexpected rot in the fascia, material delays. A bad one will tell you the project will go perfectly.
Nobody who has worked in construction for any length of time believes every job goes perfectly. If your contractor does, they’re selling you something. That’s a good time to remember the homeowner in Chicago.
About Khary Penebaker
Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership experience in construction, operations, and civic engagement.
Keep Reading
Last updated: March 25, 2026