Frequently Asked Questions

General Questions

What services does Oliwill Construction offer?

Exteriors service, renovations, remodeling, roofing, and general contracting services.

What kind of Commerical jobs does Oliwill do?
• Commercial Residential apartment; Siding, roofing, gutters, windows
• Multifamily: Duplex, fourplex, 8 unit apartments

Are you licensed and insured?

Yes. Oliwill Construction is fully licensed and insured to ensure all projects are completed safely, professionally, and in compliance with local regulations.

Do you offer free estimates?

Yes, we offer free, no-obligation estimates. Contact us to discuss your project and schedule a consultation.

How long will my home improvement project take?

Project timelines vary depending on the size and complexity of the job. After reviewing your project details, we provide a clear timeline before work begins.

How long does it take for a roof to be completed?
Roofs can be completed in 1-2 days

How long does it take to get my siding replaced?
Siding can take one week to complete

Do you work on both residential and commercial projects?

Yes, we handle both residential and commercial construction projects

Can you help with design and planning?

Absolutely. We work closely with you throughout the planning and design process to ensure the final result aligns with your vision, fits your budget, and meets your home’s specific needs.

Can I see a visual of what my home will look like?

Yes! We use advanced software like Hover to provide a realistic preview of your home, so you can see how it will look before the project begins

How do I get started with Oliwill Construction?

You can get started by contacting us through our website, phone, or email. We’ll schedule a consultation to discuss your project.

What areas do you serve?

We serve Madison & surrounding areas in Wisconsin. If you’re unsure whether we cover your area, feel free to reach out.

How do you ensure quality workmanship?

We use high-quality materials, skilled professionals, and follow industry best practices to deliver durable and reliable results on every project.

Do you provide warranties on your work?

Yes, we stand behind the quality of our workmanship and offer warranties based on the type of project completed.

Roofing: We use Owens Corning products, which come with strong manufacturer warranties for long-term protection.
Siding: James Hardie siding includes a 30-year non-prorated warranty, giving you added peace of mind and lasting durability.

Roofing Questions

How do I know if I need a roof replacement?

Signs include missing or damaged shingles, leaks, water stains on ceiling, curling shingles, or granules in gutters.

How long should a roof last?

Lifespan depends on material, asphalt shingles ~20-25+ years, metal much longer 40 –50 years, and climate.

How often should I have my roof inspected?

Most pros recommend at least once a year and after major storms. (Hail, Wind storms)

What brand of shingles does Oliwill use?

We use Owens Corning Duration® architectural shingles. These high-quality shingles are known for their durability, performance, and enhanced wind resistance, and they come with a 50-year limited warranty for long-term protection and peace of mind.

Will my homeowners’ insurance cover roof repair/replacement?

Storm-related damage often is covered, but normal wear and tear usually isn’t.

Does Oliwill help with Insurance reports?

Yes, we are able to work closely with your insurance adjusters (Agents) and meet them at the jobsite and we can communicate with them directly to help you with your project. From start to finish.

Can I replace my roof myself?

Roof work is dangerous; most homeowners hire professionals for safety and quality.

How long does roof installation take?

Depends on size and weather, often 1–5 days for a typical home.

Do you guys install skylights?

Yes, we do install skylights!

We work with Velux skylights, which are one of the most trusted and high-quality brands in the industry. Whether you’re looking to add more natural light or replace an existing skylight, we can help you choose the right option and handle the installation professionally.

When should I install Skylights

The best time to install skylights is typically during a roof replacement. Since the shingles are already being removed, it’s more cost-effective and allows for a seamless, watertight installation.

If you’re not replacing your roof, skylights can still be installed — ideally during mild weather seasons like spring or fall. This helps avoid extreme temperatures and ensures proper sealing.

If you’re in Wisconsin, planning around heavy winter weather is important, so late spring through early fall is usually ideal.

Siding Questions

How do I know if my siding needs replacement?

Look for cracking, buckling, warping, mold, loose panels, or faded/aged appearance.

What styles and materials are available?

We offer a wide variety of siding styles and materials to match your home’s look, budget, and maintenance preferences.

Common material options include:
Vinyl Siding: A cost-effective, low-maintenance option available in many colors and styles.
Fiber Cement Siding: Extremely durable and weather-resistant, designed to withstand Wisconsin’s climate with minimal maintenance.
Engineered Wood & Natural Wood Siding: Offers a beautiful, traditional wood appearance with varying levels of durability and upkeep.

We work with trusted brands such as LP® SmartSide®, James Hardie®, Norandex®, and CertainTeed®, each offering different profiles, textures, and color selections.

During your consultation, we’ll help you compare options and choose the best style and material for your home’s design and long-term performance goals.

What siding styles and materials are available?

Common options include vinyl, fiber cement, and Wood each varies in durability and maintenance. Common brands (LP, James Hardie, Norandex, Certainteed)

Will new siding improve energy efficiency?

Yes, modern siding with insulation can reduce heating and cooling costs.

How do I know if my siding will need insulation boards installed?

Once we remove the existing siding, we’re able to see what’s underneath. If we find only wood sheathing with no insulation board in place, then adding insulation boards is typically recommended. This helps improve energy efficiency and better control airflow throughout the home.

How long does siding last?

Quality siding can last 10–20+ years, depending on material and care.

Can I change my siding style or color during replacement?

Absolutely, replacement is a great time to update the look of your home.

Custom colors available, We also bring color palattes to show you examples

Can I see a visual of what my home will look like?

We use advanced tools like Hover to create a realistic visual of your home, so you can see exactly how it will look before making a decision.

Does Oliwill Construction do siding repairs?

Yes, we do siding repairs! The approach depends on the type of material and the area that needs attention.

It’s important to note that repairs may not always be an exact color or material match. To ensure the best possible outcome, we use specialized programs to identify your siding type and check if the material is still available or has been discontinued. Our goal is always to make the repair blend seamlessly with your existing siding.

Gutter Questions

How do I know if my gutters need to be replaced?

Signs include sagging, cracks, leaks, water overflowing, or pooling around the foundation.

What’s the difference between gutters and downspouts?

Gutters collect water; downspouts carry it down and away from the house.

How often should gutters be replaced?

Average lifespan is ~15–20 years depending on material and weather.

What types of gutters are best?

Seamless aluminum is popular for durability and reduced leaks.

Does Oliwill Install gutter guards?

Yes, we install Hydroflo.

Should I install gutter guards?

Many homeowners do to reduce clogs, but effectiveness varies by type/trees.

Window Questions

How do I know it’s time to replace windows?

Drafts, difficulty opening, condensation between panes, and high energy bills are common clues.

Will new windows improve energy efficiency?

Yes, modern double- or triple-pane windows reduce heat loss and lower utility costs.

How long does window installation take?

Most jobs can be completed in one day per window — total time varies by number of units.

Windows are custom ordered, it can take 4-6 weeks depending on which window you would like and then the installation 1-5 business days. Depends on the size of the job, window, project. For example 3 windows can be done in one day. If it is 30 Windows it will take 5 days.

What brands of Windows does Oliwill install?

Common brands used because of good quality and warranties in good, better best order: Lindsay, Pella, Anderson.

We can work with other specific brands that you like

Should I replace all windows at once or in phases?

Replacing all at once is often more cost-effective, but phasing is possible.

What warranty should I expect?

Windows typically come with manufacturer and installation warranties.

• Lindsay comes with Lifetime warranty
• Anderson comes with 50 year warranty
• Pella 50 year warranty

Frequently Asked by U.S. Homeowners

Do new roofs, siding, gutters, or windows increase home value?

Yes, exterior upgrades often boost curb appeal and resale value.

Can I choose my own contractor for insurance work?

Generally yes, but confirm with your insurance company first.

How can I make an insurance claim?

You can contact your insurance agent to start a claim, they will guide you through the process or we can get an intial appointment scheduled and we can help you through the process.

What should I ask a contractor before hiring them?

Ask about licensing, insurance, references, warranties, and project timeline.

Should roof and gutter work be done at the same time?

It’s common to coordinate them to minimize disruption and ensure proper water management. They can be done separately, often times it is more efficient to get them replaced together.

Proudly Serving Southern Wisconsin Communities

From Madison to surrounding towns, we bring top-quality roofing, siding, window, and gutter services to homeowners across Southern Wisconsin. Our team is committed to delivering dependable craftsmanship, personalized service, and lasting results wherever you live. No matter your location, you can count on us to treat your home with care and professionalism.