How to Choose a Contractor

A contractor is one of the larger decisions a property owner or tenant will make. Choosing the wrong one costs time, money, and peace of mind; choosing the right one means work that lasts and a straightforward process from quote to completion.

The difference between them comes down to how you evaluate before signing. This guide walks you through the steps most property managers and homeowners follow to separate contractors who are genuinely qualified from those who simply look the part.

Step Through the Process

Get at least three quotes from different contractors.
Call or email contractors in your area and describe the work you need done. Ask them to provide a written estimate that breaks down materials, labor, and timeline. Do not choose based on price alone—the lowest bid often reflects corners cut elsewhere.
Check licensing, insurance, and bonding status.
A legitimate contractor carries a state license, liability insurance, and worker's compensation coverage. Ask to see copies of their documentation. If they hesitate or cannot provide it, that is a red flag. Many states publish a searchable contractor license database online.
Ask for and call their references.
Request the names and phone numbers of three to five past clients whose work is complete and at least six months old. When you call them, ask about the quality of work, whether they finished on time and on budget, and whether they would hire that contractor again.
Look at their past work in person if possible.
Many contractors have a portfolio or can show you completed projects in your neighborhood. Seeing the actual workmanship—quality of materials, attention to detail, how edges and transitions are handled—tells you far more than a brochure or website can.
Ask about warranty and guarantee terms.
Reputable contractors stand behind their work with a written warranty that covers both labor and materials for a defined period (often one to five years, depending on the work). Get that guarantee in writing before you sign the contract.
Make sure the estimate and contract match exactly.
Before signing, compare the written contract to the estimate you received. Every detail—scope of work, materials, price, timeline, and payment schedule—should be identical. Do not sign anything with blank fields or vague language.

What It Should Look Like When Done

Completed residential roof showing professional installation with proper materials and workmanship quality — A finished roof from a qualified contractor shows proper material installation, consistent workmanship across all surfaces, clean edges and flashing, and no shortcuts in areas out of sight.

Once the work is complete, inspect the results carefully. Walk the property with the contractor and ask them to point out the work they did, the materials they used, and any details they want you to understand about maintenance or warranty. A contractor who is proud of their work will be happy to do this. The finished product should look clean, consistent, and complete—no gaps, no misaligned materials, no visible shortcuts.

What to Consider First

Attic interior showing roof structure and light penetration highlighting problem areas and moisture assessment — Understanding what your roof looks like from the inside—where light enters, where moisture collects—helps you ask better questions when contractors explain what they found during their inspection.

Before you contact any contractor, walk your property and document the condition yourself. Take photos of any visible damage, leaks, or areas of concern. Understand what the problem is in your own words before a contractor tries to sell you a solution. This clarity helps you spot whether a contractor is genuinely addressing your issue or padding the scope to increase the price.

What It Typically Costs

Pricing depends on the scope of work, local labor rates, materials, and complexity. A minor repair might cost a few hundred dollars; a full replacement can run into thousands. The National Roofing Contractors Association publishes regional cost data, and your local building department can tell you what similar permits cost in your area.

Do not assume the lowest quote is the best deal. Compare what each contractor includes in their price and ask why the estimates differ if they vary widely. A contractor who is significantly cheaper than others may be using lower-quality materials, cutting labor corners, or leaving out work that competitors included.

Payment terms matter, too. Legitimate contractors ask for a deposit—typically 25 to 50 percent—and the remainder on completion, not in full upfront. If a contractor demands full payment before starting, that is another warning sign.

The Options Compared

Contractor Type	Licensing & Insurance	Best For	Risk Level
Licensed and insured company	State license, liability insurance, bonding	Major projects, roofing work, structural repairs	Low
Licensed independent contractor	State license, often has insurance	Smaller projects, repairs, specialized work	Medium
Unlicensed handyperson	Usually none	Not recommended for significant work	High
Licensing requirements vary by state and by the type of work. Check your state's contractor licensing board or building department to confirm what your jurisdiction requires.

Before You Sign

Before signing anything, it is worth checking a contractor's standing for yourself. You can do that at the Better Business Bureau, which lists accreditation status and any unresolved complaints. A quick search takes five minutes and can save you from a contractor with a pattern of problems.

Once you have chosen a contractor and are ready to move forward, make sure your contract includes the full scope of work, a start and completion date, the total price and payment schedule, warranty terms, and a cleanup plan. Get everything in writing. Verbal agreements disappear quickly when a dispute arises.

Learn From the Experts

If you want to hear from a contractor directly about what to look for, this guide covers the essentials: