Real Estate

When I underwrite a property with obvious deferred maintenance, the first question I ask myself is not “how much will the repairs cost?” but “how will the market re-price the asset?” Repairs matter because they affect cash flow, liability, and a buyer’s required return. In practice the market responds not only by reducing near-term NOI but by increasing the cap rate a buyer applies — a cap rate “haircut” that’s often larger...

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When I started evaluating office-to-residential conversion deals several years ago, I quickly realized they live at the intersection of three disciplines investors frequently underweight: zoning and land-use law, construction feasibility, and rent/market economics. You can't simply take a mid-rise office block, slap in some kitchens and call it a day. The devil — and the value — is in the details. In this piece I walk through the practical...

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When I first started analyzing rental properties, I treated the math on paper like it told the whole story: purchase price, rent, mortgage payment, taxes, and a tidy cap rate. Reality, as I learned the hard way, is messier. Maintenance, vacancies and capital expenditures (CapEx) quietly erode returns in ways that aren’t obvious from purchase spreadsheets or flashy listing photos. In this article I’ll walk through the hidden cost categories...

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I review syndication offers regularly, and one thing I’ve learned is that the headline returns rarely tell the whole story. When sponsors pitch a deal, they often lead with attractive IRRs or projected cash yields — but the promise on paper can hide complex distribution mechanics, sponsor incentives, and dilution risks that materially change my realized return. In this piece I’ll walk you through how I evaluate a syndication offer,...

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Interest rate moves are the kind of macro event that feel abstract until they show up in your bank account or property valuation reports. Over the last decade I’ve watched several rate cycles and advised investors on how to adapt underwriting, debt management, and asset-level operations. In this piece I want to walk you through precisely when rising rates really bite commercial real estate (CRE) values, what drives the timing and magnitude of...

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Why rental yield and inflation matter — and why the simple answer rarely worksI get asked a version of the same question a lot: “What rental yield do I need to beat inflation in my city?” It’s an important question, because inflation quietly erodes the purchasing power of rent checks and property values alike. But the answer isn’t a single number you can apply everywhere. The yield you need depends on your financing, taxes, local...

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