How to stress-test short-term rental income in your city using occupancy shocks and market comps to decide between Airbnb and long-term leasing

I often get asked whether the same valuation metrics apply when comparing single-family rentals (SFRs) in secondary markets versus primary markets. The short answer is: the metrics themselves are the same, but their relative importance, interpretation and the assumptions you attach to them should change based on market context. Below I walk through the specific metrics I use, how I adjust them between market types, and practical ways to test...

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I hunt for gains, but I also focus on the messy, underappreciated side of investing: taxes. Over the years I’ve used tax-loss harvesting (TLH) as a pragmatic tool to reduce tax drag in taxable accounts. Doing it well across multiple taxable accounts — and when you’re rotating into similar ETFs rather than identical ones — requires clear rules, careful record-keeping, and a dose of common sense. Below I walk through how I harvest losses...

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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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Generating steady income from options is attractive: premium flows, time decay working in your favor, and a wide menu of strategies from covered calls to credit spreads. But the same leverage and asymmetric payoff that make options lucrative also create concentrated downside risk if you size positions poorly. I approach options income the same way I approach real estate or equities: start with clear allocation rules, measure potential loss, and...

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I often get questions from readers who are approaching retirement with a relatively small nest egg and a big fear of sequence-of-returns risk: “How can I avoid a large drawdown in the early years of retirement?” Volatility targeting is one practical technique I use and recommend to help smooth drawdowns while keeping a meaningful allocation to growth assets. In this article I’ll walk you through what volatility targeting is, why it matters...

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I run scenario analysis on my clients’ retirement plans like a pilot runs checklists before takeoff: it’s not glamorous, but it’s the thing that prevents disaster. When I talk about a portfolio’s “glidepath” toward retirement income, I mean the path your asset allocation, expected returns, volatility, and withdrawals together create as you transition from accumulation to distribution. Scenario analysis doesn’t predict the future....

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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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I’ve helped investors and real estate owners quantify risk and design practical hedges for years, and one of the most common problems I see is a concentrated stock position — often an employee with most of their net worth parked in one company. Options are a powerful, flexible tool to reduce that tail risk without necessarily selling shares and triggering a taxable event or giving up upside. Below I walk through the approaches I use and...

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