Choosing Between Three Contractors Without Guessing

Three estimates on the kitchen table are only comparable if they describe the same job. Most of the time they do not, which is why the totals sit thousands of dollars apart and the homeowner ends up choosing on gut feeling. The way out is not more quotes. It is a fixed set of questions applied to all three.

What follows is a decision framework. It assumes you are spending somewhere between $10,000 and $40,000 and that you would rather understand the difference than be reassured about it.

Step one: hand out the same scope

Before anyone measures your house, decide what you are asking for. Not the brand — the scope. For a roof that means tear-off versus overlay, how many layers come off, whether ice and water shield goes at the eaves and in the valleys, drip edge on rakes and eaves, ventilation work, and what happens to the gutters. For siding it means whether house wrap is being replaced, how window and door openings get flashed, and whether trim is included. For windows it means insert or full-frame.

Then give every company the same list and ask them to price it. If one of them tells you the list is wrong, that is useful — ask why, and carry the answer to the other two. A contractor who improves your specification is showing you something a total never will.

The specification lines that move the price

These are the items that separate a $14,000 roof from a $22,000 roof on the same house:

• Number of layers removed and whether disposal is included
• Ice and water shield coverage, by location and width
• Underlayment type across the field
• Nails per shingle, and whether the nail zone is specified
• New drip edge and new pipe boots, or reused ones
• Valley detail, step flashing at walls, chimney flashing and counterflashing
• Ridge vent length and whether the deck slot is being cut
• Warranty level being registered

We cover the line-by-line reading of a roofing bid in more detail in our guide on how to read a roofing quote, so this post stays on the comparison itself.

Step two: check registration and insurance, not logos

In Connecticut, home improvement work is done under a Home Improvement Contractor registration. Ask for the number and look it up. A certification badge from a manufacturer is a separate thing — it means the company has met that manufacturer's training and standing requirements, which is what allows certain extended warranties to be offered. Both matter, for different reasons, and one does not substitute for the other. Our explainer on Connecticut contractor registration walks through what the registration does and does not guarantee.

Insurance is the item most homeowners skip. Ask for a current certificate showing general liability and workers compensation, issued by the insurer rather than typed by the contractor. If a crew member is hurt on an uninsured job, the exposure can land on the property owner. This is a two-minute request that changes the risk profile of the whole project.

Step three: settle who pulls the permit

Roof replacement requires a building permit in every town we serve, and only a registered Home Improvement Contractor can pull it on your behalf. If a bid is silent on the permit, ask directly whether the fee is included in the number you are looking at, because permit fees are set by each town and normally calculated against the value of the job.

Siding and window replacements work differently. Most Connecticut towns do not require a permit for a straightforward like-for-like replacement where openings are not changed. A permit generally becomes necessary once the scope grows — exterior insulation, sheathing replacement, resized openings, or structural repair discovered after demolition. The details are in our post on roof and exterior permits in Connecticut.

Be wary of any suggestion that you pull the permit yourself as the homeowner to save money. That moves responsibility for the inspection onto you.

Step four: compare against the code numbers for your town

Appendix AY of the 2022 Connecticut State Building Code assigns every municipality an ultimate design wind speed (Vult) and a ground snow load (pg). These are public figures, and they are the fastest way to tell whether a contractor is quoting to your house or to a state average.

Two things worth knowing. The central shoreline towns of Guilford, Madison and New Haven carry a higher design wind speed than the Fairfield County shoreline, because the figure tracks exposure to open water rather than distance from New York. And a shingle's advertised wind rating only holds if it is fastened the way the manufacturer requires to earn it, which for high-wind coverage usually means six nails per shingle in a defined nail zone instead of four.

One clarification, because it gets misquoted in sales conversations: the code's high-wind underlayment attachment trigger above 110 mph is keyed to Vasd, the allowable stress design wind speed, which works out to roughly 93 to 97 mph in these towns. It is not keyed to Vult. So a contractor citing your 125 mph figure as the reason a special underlayment fastening schedule is mandatory has the wrong number. There may be good reasons to upgrade an underlayment on a shoreline house. That is not one of them.

For windows, the checkable number is on the NFRC label. All of Connecticut is in the ENERGY STAR Northern zone, which under version 7.0 requires a U-factor of 0.22 or lower and a solar heat gain coefficient of at least 0.17. SHGC is a minimum, not a maximum — in a heating climate, a window that blocks too much solar gain is throwing away free winter heat. Any window bid should state both figures for the unit being quoted.

Step five: ask what happens when they find something

On a tear-off, some percentage of the time the deck underneath is soft, or the sheathing behind the siding is wet. The honest question is not whether that will happen. It is how it will be priced when it does.

Ask each contractor for a unit price in writing: a rate per sheet of plywood, a rate per linear foot of replaced rafter tail or fascia. Ask whether you will be told before the work is done or after. A bid that handles hidden damage with a stated unit price is more predictable than a lower bid that leaves it open, even though the open bid looks cheaper on the day you compare them.

Step six: read the warranty as two documents

There is a manufacturer's material warranty and there is a workmanship warranty, and they cover different failures. Material warranties run up to 50 years limited lifetime on GAF roofing and 30 years non-prorated on James Hardie siding. Extended coverage that includes installation, such as the GAF Golden Pledge, is available only on qualifying projects from certified installers.

When you compare, put them side by side:

What to expect from the estimate visit itself

Someone comes to the house, measures, looks at the attic and the existing condition, and gives you a written itemized price. It is a sales appointment, and treating it as one is fine — you are the one collecting information. Bring your scope list. Ask the six questions above out loud and write the answers down while the person is standing there.

If the three bids still land far apart after all this, the gap will now have a name: a different underlayment, a different nail count, sheathing included in one and excluded in another, or a full-frame window replacement priced against an insert.

We work across 15 Connecticut towns on roofing, siding and windows, and we would rather be compared on specification than on a round number. When you are ready for a written price on a defined scope, request an estimate and we will come measure and put it in writing.