Roof replacement looks straightforward from the street: tear off old shingles, put on new ones, haul away debris. Up close, it’s a choreographed sequence with dozens of decisions that affect performance, longevity, and cost. Homeowners who understand the steps make better choices and avoid the stress that comes with surprises. This is the practical, field-tested walkthrough we use at Ready Roof Inc., built from years on ladders across Milwaukee County and the surrounding communities.
What prompts a full replacement
Most roofs die of a combination of age and water. The top layer tells part of the story, but the real decision often hinges on what you find underneath.
I’ve stood in attics with homeowners on a 92-degree day, flashlight beams bouncing off rafters, pointing out faint coffee-colored halos on the decking. Those rings come from a winter of condensation or minor leaks and they matter. On the outside, you might see shingles curling at the corners, granules collecting at the base of downspouts, exposed fiberglass mats, or dark lines tracing along nail heads. Hail and wind can accelerate all of this. In southeast Wisconsin, we see storms that punish south and west slopes. A roof may be fine on one side and failing on the other.
When repairs stop making sense, it’s usually for one of three reasons. First, the shingles are at the end of their rated life and are brittle or cupped, so patching becomes a band-aid. Second, leaks trace to multiple causes, like flashing fatigue, nail pops, and underlayment failure, and a single repair can’t address the system. Third, there’s underlying deck damage. If you can push a screwdriver into the sheathing without much resistance, it’s time to think replacement.
The planning conversation
Every successful replacement begins with a frank conversation about priorities. Some homeowners want the longest possible warranty. Others care most about curb appeal, noise during installation, or timing around a family event. We sit down at the kitchen table, pull out photos, run through material options, and separate needs from wants.
Budget is a constraint, but it’s also a tool. For example, if the roof is a simple gable with good ventilation, an architectural asphalt shingle may be the value sweet spot. If the home has low-slope sections, dormers, and valleys that collect snow, we may steer you toward upgraded ice and water protection in risk zones rather than a wholesale move to premium shingles. We talk underlayment types, attic airflow, and flashing metals. We consider the neighborhood’s look and, yes, HOA rules if they exist.
We also call out the realities of Milwaukee weather. Replacements can proceed in the shoulder seasons. If the nightly low dips into the 30s, we plan staging so adhesives have daylight warmth to activate. If a cold front arrives mid-project, we phase tear-offs so the home isn’t exposed overnight. Communication here is everything.
Inspection that goes beyond shingles
The exterior walkthrough covers more than the roof field. We photograph and measure, of course, but we also note tree overhangs, satellite dishes, old mounts that no one remembers, and chimney condition. Chimney counterflashing that looks intact from 20 feet away often shows hairline cracks up close, especially on brick chimneys that absorbed years of freeze-thaw.
Inside, we check the attic. Baffles at the eaves, clear intake vents, and unobstructed exhaust are not bonus features. They are what keep a roof cool in summer and dry in winter. I’ve seen brand-new shingles fail early because moisture trapped in the attic cooked the deck from below. If the insulation is Click for source blown-in cellulose sitting against the soffit edge, we plan for baffles or airflow chutes before we replace. If a bathroom fan vents into the attic, we reroute it outside.
We also listen for soft spots underfoot during measurements. Decking should feel uniform. A springy step near a valley or along the eave usually means hidden rot. We flag those areas, estimate replacement sheets, and include them in the plan.
Choices that shape performance
Roofing is a system. Think of it as layered armor that sheds water, breathes, and manages temperature. Each component plays a role.
Shingles. Architectural asphalt shingles dominate for a reason. They balance cost and durability, resist wind uplift better than three-tab shingles, and carry color blends that mimic wood shakes. Not every “30-year” shingle is created equal, though. Some brands handle nail strip design better, which speeds installation and reduces the chance of high fasteners that can cause later leaks. If you want another look and lifetime longevity, metal and synthetic composites exist, but they come at a higher price point and can change the home’s character.
Underlayment. Traditional felt works but has drawbacks when it gets wet. Synthetic underlayments resist tearing and provide a safer walking surface for crews. In ice-prone zones, self-adhered ice and water shield is non-negotiable at eaves, valleys, and around penetrations. In our climate, we extend ice and water protection at least 24 inches past the warm wall, often more on low slopes.
Ventilation. Intake at the eaves, exhaust at the ridge. That’s the formula. Ridge vents paired with continuous soffit vents create balanced airflow. Box vents can work on complex roofs where ridge length is limited, but they must be calculated to match intake. Without balance, you get negative pressure that pulls conditioned air and moisture into the attic.
Flashing and metals. Step flashing along sidewalls, counterflashing at chimneys, and L-flashing at headwalls all deserve new metal during replacement. Reusing old flashing to save a few dollars often leads to callbacks. For valleys, open metal valleys with W-shaped center ribs shed debris better than closed valleys in homes with heavy leaf fall. Drip edge at eaves and rakes helps guide water into gutters and protects the deck edge from capillary action.
Fasteners. Nails are small but critical. We use ring-shank nails for better holding power and fasten within the shingle’s manufacturer-defined nail zone. Too high, and the course below won’t bond correctly. Too low, and nails can be exposed to water.
Permits, scheduling, and neighbors
The city or village may require permits and inspections. We pull them and schedule inspections so they don’t disrupt momentum. Good scheduling anticipates materials arriving at least a day before tear-off, with a weather window that avoids significant rain. We notify neighbors, not just as courtesy, but to protect vehicles and plan for street parking. Nothing sours a project like a neighbor finding a nail in a tire because no one thought to ask them to park a bit further down the block.
We also plan staging. Where will the dumpster sit? How do we protect the driveway? We use protection boards and watch for low-hanging power lines. If the home has a stamped concrete patio, we edge it with foam and plywood where debris might land.
Tear-off with surgical care
The gut of the work is tear-off. A well-run crew removes material quickly without turning the yard into a minefield. We start at the ridge and work down, section by section, keeping the roof watertight as we go. On a simple, single-story ranch, tear-off might finish before noon. On a two-story with multiple dormers and layers of old shingles, it can take a day and a half.
We use magnetic sweepers constantly, not only at the end. Tarps catch most debris, but plywood shields and temporary chutes control where material falls. Satellite dishes get removed and reinstalled or relocated with owner approval. Old vents and pipe boots come off, exposing penetrations that we’ll reseal correctly.
Once the roof is bare, we inspect the deck. We replace any sheathing that shows rot, delamination, or mold. Edges at the eaves and around penetrations are frequent offenders. If we find more damage than expected, we pause and walk the homeowner through options and costs before proceeding. Surprises happen, but they should never be invisible line items.
Rebuilding the roof as a system
Installation begins with details that do not show from the street but determine long-term performance. We set drip edge at the eaves first, then install ice and water shield, running it up the roof to the calculated line. Valleys and penetrations receive ice barrier next. On cold mornings, we stage the rolls in the sun so the adhesive bonds cleanly.
Synthetic underlayment covers the remaining field, lapped and fastened per manufacturer specs. This is where pacing matters. If weather threatens, underlayment alone can keep the home dry overnight. Crew leads make the call on where to stop so the day’s work ends on a watertight boundary.
Starter shingles go on at eaves and rakes, with sealant strips oriented to the edge. That sealant locks the first course against wind. We snap chalk lines to keep courses straight, especially on roofs visible from the street at a shallow angle where even small deviations show.
Valleys get their treatment next. On an open metal valley, we keep the shingle cut lines uniform, typically exposing 3 to 4 inches of metal. We seal and fasten outside the valley center, leaving the water pathway clear. Step flashing along walls ties into the shingles, one piece per shingle course, never a long continuous strip. Chimney work involves counterflashing cut into mortar joints, not surface-applied metal with caulk. The latter fails; the former lasts.
For ventilation, we cut the ridge slot to the manufacturer’s width, leaving uncut sections above hips or near ridge ends where structure requires. Ridge vent installs after shingles, with cap shingles nailed over it at prescribed spacing. In homes without adequate soffit intake, we discuss adding vents or, if needed, smart solutions like edge vents that introduce airflow where soffits are closed.
Pipe boots and accessories round out the field. We prefer boots with reinforced collars, especially on homes where PVC moves slightly with temperature swings. Every penetration is a potential leak, so every penetration gets extra care: ice membrane, correct flashing overlap, sealant only as secondary protection.
What the day looks like at your home
On installation day, crews arrive early. The foreman introduces the team, reviews the plan, and walks the property with you. We protect landscaping with breathable tarps that won’t cook plants in summer sun. We move grills, furniture, and delicate planters when possible, with your permission, and note their location to put them back.
Noise is part of the day. Tear-off sounds rougher than installation. Pets and young children often need a plan. We arrange break times when you need quiet. Power tools draw from our cords and generators, not your garage GFCIs that trip under load. We keep gates closed if you have pets and check that doors and windows are sealed against dust.
Deliveries come pre-dawn or early morning. The loader lifts pallets of shingles to the roof to minimize lawn traffic. If your driveway is steep or fragile, we hand-load or stage pallets off to the side. When a summer storm pops up unexpectedly, we cover open areas with tarp and shift to protected sections or indoor prep tasks. The goal is steady progress without compromising the home.
Clean-up that respects your property
The best compliment after a replacement is a yard that looks untouched. Cleanup is not a quick sweep. It happens in layers. We pick up large debris continuously, sweep patios and walks, and run rolling magnets across grass, beds, and driveway multiple times. Gutters get cleared of shingle granules and nails. We check downspouts for lodged debris and flush them if needed.
The crew lead does a final walk with you. We inspect attic spaces for daylight where there shouldn’t be any and check that bathroom fans, kitchen vents, and dryer vents exhaust outside. If we reinstalled a satellite dish, we test the signal. We label any paint touch-ups or small caulk smears that need cleaning, then handle them before we call it complete.
What drives the price
Price follows complexity. The number of facets, valleys, and penetrations affects labor. Steeper pitches require harnesses and staging that slow production. Multi-layer tear-offs add disposal costs and time. Then there are material choices: a standard architectural shingle with synthetic underlayment and ice barrier will cost less than a premium impact-rated shingle with copper flashing and open metal valleys.
Permits, dumpster fees, and deck repair allowances add real dollars. A typical allowance might include two to four sheets of OSB replacement, with additional sheets priced per piece. If we anticipate more, we tell you up front. Seasonal demand can nudge prices. After a wind or hail event, material lead times lengthen. We keep quotes valid for a set period and note any potential volatility.
Insurance work brings another layer. If a storm caused damage, we document with photos and, at your request, meet the adjuster on site. We talk in scope language rather than line-by-line brand choices. The goal is to build a complete scope that restores the roof to its pre-loss condition or better, with code-required upgrades included.
How long it really takes
A straightforward, single-layer, walkable roof on a ranch often finishes in one day. Add hips, valleys, dormers, and steep pitches, and you’re looking at two to three days. Deck repairs add time but prevent problems later. Weather can add a day. We plan work so the roof never sits open overnight. That means we might push certain sections to the next morning rather than rush and risk exposure.
We also factor in inspection timing if your municipality requires a mid-project look. We coordinate so you do not have to take multiple days off work. Most homeowners can stay in the house during replacement. If you work from home and need periods of quiet, tell us. We can sequence loud tasks around your schedule within reason.
Aftercare, warranties, and what to watch
A new roof isn’t a “set and forget” item. It needs simple, periodic attention. Gutter cleaning in fall and spring keeps water moving. A quick visual check after major storms can catch dislodged shingles or wind-driven debris. If you see a shingle tab flipped up or a small section lifted along a ridge, call us. Early fixes prevent bigger issues.
Manufacturer warranties cover materials against defects, while the contractor’s warranty covers workmanship. We register your shingle warranty and provide documentation. Keep it with your home records. If you plan to sell within a few years, transferable warranties can add value. We explain what is and isn’t covered so there are no assumptions later.
Your attic remains part of the system. If you add insulation, make sure baffles aren’t buried. If you remodel and add bath fans, vent them outside, not into the soffit cavity. Seasonal ice along eaves can still occur in extreme conditions, but a well-ventilated, well-insulated attic reduces the risk significantly.
Trade-offs and edge cases we see often
Low-slope transitions. Sections that look flat but measure between 2:12 and 4:12 require special attention. Many shingles are rated down to 2:12 with specific underlayment layers. In practice, if the section collects drifting snow, we recommend a low-slope membrane. It costs more per square foot but performs better long term.
Historic homes. Older homes have plank decking instead of modern OSB. Gaps between planks can exceed manufacturer specs for shingle fastener support. We sometimes add a layer of sheathing over planks for Ready Roof Inc. a stable base. It adds cost but gives nails consistent bite and prevents telegraphing.
Tree coverage. Shade is nice for summer bills but tough on roofs. North-facing slopes with overhanging branches accumulate moisture and organic growth. We suggest trimming limbs back at least 8 to 10 feet and choosing shingles with algae-resistant granules. Expect more frequent cleanings, not power washing, which strips granules, but gentle chemical treatments when necessary.
Snow country details. Ice and water shield should extend beyond code minimums in areas with consistent ice dam history. Heated cables are a last resort, not a first solution. Address insulation and ventilation first, then consider cables for unique architectural traps.
Metal flashings versus caulk. Caulk ages, metal persists. Whenever we have a choice, we solve water paths with formed metal and correct overlaps. Sealants serve as a backup. If you’ve been told “we’ll caulk it,” ask for a metal detail instead.
A simple homeowner prep checklist
- Clear vehicles from the driveway and garage to allow dumpster and material delivery. Move fragile yard items, planters, and grills away from the house perimeter. Mark irrigation heads and garden lighting near the foundation if possible. Notify neighbors about the project dates and ask them to avoid parking near the home. Keep pets and kids indoors or off-site during active tear-off hours.
Why Ready Roof Inc. emphasizes transparency
The best roofing jobs look effortless because the hard thinking happened early. Our crews are local, and we build for this climate. That means more ice barrier where it counts, ventilation balanced to your attic, and flashings that solve water paths instead of hiding them. We document before, during, and after, not to flood you with images, but to give you confidence in what’s under the shingles you’ll never see again.
Most importantly, we aim for control of variables. Weather, supply chains, and hidden deck issues will always add uncertainty. Experience narrows the band of surprises. Communication closes the rest.
A homeowner’s story from Elm Grove
A homeowner on a tree-lined street near Elm Grove called after noticing a faint stain along a second-floor ceiling. The roof was 18 years into a 30-year shingle. From the ground, it looked fine. Up close, we found granule loss concentrated along the north valley and chimney flashing that had separated at a mortar joint, likely during a winter freeze.
In the attic, the deck showed minor staining around the valley line. We proposed a phased plan: targeted tear-off along the valley and chimney with full replacement in two years, or a full replacement now including upgraded valley metal and new chimney counterflashing. They opted for the full job. During tear-off, we replaced three sheets of deck where moisture had crept in. We extended ice and water shield well past the warm wall and added continuous ridge venting to match newly cleared soffits. That ceiling stain never returned, and their winter energy bills dropped because the attic no longer trapped heat and moisture.
The result you should expect
A finished roof should look clean, with straight lines, snug flashing, and ridge caps that sit evenly. Gutters should run clear and align under drip edges that guide water. In the attic, you should see daylight only at the ridge vent, not along eaves or penetrations. On a windy day, you should not hear flapping or see shingle edges lift. After a heavy rain, there should be no drips or damp smells indoors. These are simple tests, but they tell the truth.
Good roofing is not magic. It is method. It’s measuring twice before you cut once, putting metal where water wants to go, and respecting the building’s need to breathe. When done right, you won’t think about your roof again for a long time.
Contact and next steps
If you want a straightforward assessment or you’re weighing repair versus replacement, we’re happy to walk the roof with you and explain what we see. Clear photos, plain language, and a plan that fits your priorities go a long way toward making a big project feel manageable.
Contact Us
Ready Roof Inc.
Address: 15285 Watertown Plank Rd Suite 202, Elm Grove, WI 53122, United States
Phone: (414) 240-1978
Website: https://readyroof.com/milwaukee/
We can usually schedule evaluations within a few days, even during busy seasons. Bring your questions. Bring your concerns. We’ll bring ladders, cameras, and the experience to lay out a roof replacement process that doesn’t leave you guessing.