25% more $, but 400% better outcomes
New Roof Part 3
With the asbestos removal, roof demolition, and masonry repair behind us, we were ready to move to the most precarious stage of the roof build. We had to cut away much of the old roof’s structural support to add the new roofline. This work would involve both the architect and the engineer for guidance. In situations like this, the contractor needs to take a step back and follow the lead of the engineer and architect. Messing this up could lead to structural collapse and possibly injuries. So we received very specific instructions and plans from the engineer.
In our case we had one not‑so‑simple issue. On the north side of the building, we needed to cut all the roof rafters along the north wall to make room for the wall we had to build up to support the new raised roof. The plan was to put the new roof above the old one, enclose the building for winter, and demolish the old roof inside the new space. The challenge was taking the load off the wall so we could cut the beams while safely transferring that load to the rest of the structure. The image that follows shows the inside of the north wall. Light streamed in through the opening where we removed the sheathing in preparation. Below the windows is the new ledge board to carry the load of the new wall and roof.
The key to pulling off this re‑roofing was to transfer the load from the main roof beam. The old roof system was simple: long rafters attached into the brick wall at both ends with a central beam running the length of the building to support the rafters. In the image below, the central beam is highlighted with a red line. Under that beam and perpendicular to it is a new 2x6 wall designed to spread the load off the main beam. Lucky for us, this old building was built to last centuries.
Once the load had been spread, it was time to cut the beams and build the new extension of the north wall. Unlike the south wall, which needed to be made of brick to comply with building code for fireproof property‑line walls, the north wall extension was wood framed. Spanning the north and south walls were the engineered timber I‑beam roof joists. Getting these long beams on site and hauled up to the roof was no small task, but unlike natural timbers, these are manufactured to length and will never bend, warp, or curl.
At the front of the building, where the roof meets and covers the cornice, we focused our efforts next. After removing the roof and cleaning out the top of the cornice, it became clear that the brick wall behind the cornice would have to be built up to provide additional support. Moreover, the internal wood structure that held up the cornice’s roof also had to be rebuilt. The cornice is one of the most prominent features of this architectural style, which added even more complication as we now needed to build a gutter into our refurbished cornice.
With all of the structure in place, it was finally time to close up this old beauty. We had removed the original roof back in September of ’25. Since then, the main building had been covered in plastic tarps and the carriage house had been left to the elements. Because we were demolishing and rebuilding most of the carriage house, nature’s course would only make it easier to take down that structure. That said, we were quickly approaching winter and needed to make sure the weather did not cause additional damage.
Roofs are one of the last places any investor should look to save money. Roofs are expensive to fix and are prone to high labor costs—especially when the roof is over five stories up and the worksite is in a crowded downtown location. Things get expensive very quickly. That is why investing in high‑quality materials is more about preventing future maintenance costs than anything else. Sure, we could use cheap plywood, tar paper, and shingles, but doing things for the long term now will probably increase the cost by about 25% while likely increasing the lifespan of the roof by 300% to 400%. For long‑term investors, it’s a no‑brainer.
As a side note, it’s worth acknowledging that many quality‑first construction practices run directly against the incentives that drive most financial investors. When your business model depends on turning a property in twelve to thirty‑six months, the difference between a material that lasts twenty years and one that lasts fifty is irrelevant. The investor won’t be around to deal with the failure, so their rational move is to buy the cheapest option that will survive inspection and hold together long enough to close. It’s not ignorance; it’s the predictable outcome of a system that rewards short‑term gains and ignores long‑term liabilities. Pro‑forma models rarely account for reduced maintenance costs or extended service life, so those benefits never show up in the spreadsheet. What does show up is the immediate hit to the budget when you choose better sheathing, higher‑grade shingles, or corrosion‑resistant fasteners. And when the spreadsheet is the only thing steering the ship, the default becomes doing the bare minimum required to sell the asset and move on.
But that logic only serves people who never intend to live with the consequences of their decisions. Owner‑operators don’t have that luxury. If you plan to hold a property for years or decades, the “minimum viable product” mindset becomes a liability. Cheap materials fail early, create cascading problems, and force you into a cycle of constant patching that quietly drains time, money, and attention. The big institutional players can afford to think in quarters; you can’t. If you want a building that stays dry, stable, and low‑maintenance, don’t copy the habits of investors who are already planning their exit. Build for the person who will still be dealing with the roof ten winters from now, because that person is you.
In the following posts in this series, we will cover demolishing and removing the old roof joists, securing the north wall addition, and shingling the roof. But before we move on, it’s worth pausing on the real lesson buried in this phase of the project: small, intentional upgrades in materials can produce outsized returns in durability, safety, and long‑term cost control. Spending an extra 10–25% on better sheathing, straighter lumber, corrosion‑resistant fasteners, or higher‑grade shingles isn’t about luxury, it’s about engineering a roof that lasts decades longer and demands far fewer emergency interventions. The math is simple: a roof that needs patching every few years quietly drains time and money, while a roof built with materials that resist moisture, movement, and UV breakdown pays for itself many times over.
If you want to apply this thinking to your own projects, start by identifying the components most exposed to weather or structural stress and upgrade those first. Choose sheathing with proper exterior ratings, shingles with proven wind and impact resistance, and fasteners designed for that specific job. Inspect every board before it goes up, reject anything that’s warped or wet, and store materials properly so they don’t fail before installation even begins. On the management side, sequence the work so nothing gets rushed—good materials only perform well when they’re installed under the right conditions. These small decisions compound into a structure that stays tight, dry, and low‑maintenance for years, turning a modest upfront premium into a long‑term win.
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