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CASE STUDY — MULTI-FAMILY - NAPLES, FL

Cherry Oaks

A flawed roof design caused widespread leaks across multiple buildings — CWC partnered with a roofing consultant to redesign the system, install advanced drainage crickets, and deliver a durable, energy-efficient roofing solution ahead of schedule.

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The Challenge

Addressing Design Flaws Across Multiple Buildings

The Cherry Oaks community in Naples, Florida was experiencing persistent leaks across several buildings due to a flawed original roof design by another contractor. These widespread issues required a comprehensive solution that addressed the root cause of the problem and restored proper drainage and function for the entire multi-family property.

The widespread leaks caused by the flawed roof design created challenges across multiple buildings. Crews had to diagnose issues that were affecting the entire community and work efficiently in a multi-structure environment without disrupting residents or interrupting daily activity. To ensure accuracy, CWC collaborated closely with a roofing consultant to understand the full extent of the design problem.

To add to the challenge, Naples’ intense rain events made proper drainage absolutely critical. The existing roofs were not directing water correctly, which required careful removal, detailed documentation, and the construction of custom cricket systems to resolve long-standing water flow issues throughout the community.

The multi-building leaks at Cherry Oaks presented a major challenge for both the homeowners association and the CWC team. A flawed original design had caused drainage failures across numerous roofs, resulting in persistent water intrusion during Naples’ intense rain events. To fully understand the scope of the problem, CWC collaborated closely with a roofing consultant to conduct a detailed assessment and identify the root cause.

Addressing these widespread issues required more than simple repairs — it demanded a complete redesign of critical roof areas. CWC engineered and constructed a custom system of crickets to correct drainage problems, improve water flow, and restore the overall functionality of the roofing system. This solution required careful planning and precise craftsmanship to ensure long-term performance across every affected building.

THE SOLUTION

CWC designed and installed a durable, problem-solving roofing system

To address the persistent leaks across multiple buildings, CWC worked closely with a roofing consultant to design an advanced system of crickets that improved drainage and overall roof function. With careful planning and coordination, our team framed and constructed this system while installing a 2-layer Polyglass underlayment and new flashings throughout the community.

The project included Eagle Capistrano Concrete Tile in a 2-color blend for style and durability. Our crews maintained constant communication with the homeowners association, used drone technology to document progress, and ensured that every step of the installation met high standards of quality and efficiency. This approach delivered a reliable, long-lasting roofing solution that restored the entire community and gave residents confidence in the system for years to come.

Fast, precise work with minimal disruption ​

Time management and careful planning were critical to the Cherry Oaks project. The CWC project management team coordinated every step of the roof replacement to ensure the work was completed safely, efficiently, and with minimal disruption to residents across the multi-family community.

Thanks to our experience and detailed project planning, CWC successfully completed:

  • The design and construction of an advanced cricket drainage system.

  • The installation of a 2-layer Polyglass underlayment, new flashings, and Eagle Capistrano Concrete Tile throughout the development..

To achieve these results ahead of schedule, CWC deployed a skilled crew, utilized drone technology for progress documentation, and maintained strict safety protocols on-site daily. The project was completed efficiently, leaving the buildings with a durable, aesthetically pleasing roof system that restored functionality and gave residents confidence in their community’s infrastructure.

Prioritizing the well-being of residents and crew

With multiple buildings and a complex roofing system to install, safety was the top priority throughout the Cherry Oaks project. CWC maintained a constant focus on protecting both residents and our crew members during every phase of the installation.

We implemented safety perimeters around each building, stationed monitors on the ground, and used cones to guide pedestrian traffic. All crew members working on roofs were roped and harnessed according to OSHA standards. These precautions ensured that everyone — residents and workers alike — remained safe while allowing the team to complete the project efficiently and without incident.

Roofs built to last

At Cherry Oaks, CWC didn’t just fix the leaks — we installed a durable roofing system designed to improve function and protect the buildings for decades. Using high-quality materials, including a 2-layer Polyglass underlayment, new flashings, and Eagle Capistrano Concrete Tile, we ensured long-term protection against heavy rain events and general wear.

Our experienced superintendents oversaw the project to make sure all systems were installed to code and according to manufacturer specifications. Residents and the homeowners association can now feel confident that their roofs are not only visually appealing but also built to last, providing reliable, worry-free performance for years to come.

 

Keeping clients informed every step of the way

Large projects like Cherry Oaks come with complex logistics, multiple buildings, and design challenges that require careful planning and coordination. CWC’s team has the experience and know-how to adapt to any job site, ensuring work progresses smoothly and efficiently.

Throughout the project, we maintained daily communication with the homeowners association and used drone photography to document progress, keeping residents — including those living out of state — informed at every step. Our field management team adjusted quickly to challenges, ensuring the project stayed on schedule, on budget, and met the client’s expectations for quality and functionality.