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’ve been asked many times whether a robo-advisor such as Betterment can replace a core taxable allocation in a long-term portfolio. The short answer is: it depends. But that answer isn’t useful without unpacking the trade-offs — particularly tax drag, asset location, and performance nuances — so I’ll walk through how I evaluate this in practice and what I’d consider before moving a large taxable sleeve into any automated...

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I often get asked by investors whether tapping home equity with a HELOC or doing a cash-out refinance is the smarter move — especially when the real goal is to preserve or even improve portfolio returns. I've run the numbers for clients, run scenarios for my own planning, and weighed the trade-offs this article lays out. Below I walk through how each option works, the cost and risk implications for an investment portfolio, and practical...

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I’ve evaluated dozens of multifamily deals over the years, both as a solo investor and as a passive participant in syndications. Deciding whether to lead a purchase on your own or to join a multifamily syndication is not just about capital — it’s about time, skills, risk tolerance, and the quality of the sponsor. Below I share a practical checklist and the decision framework I use when weighing syndication opportunities versus buying solo....

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I often get asked how to generate reliable, predictable income from an equity portfolio without surrendering long-term growth. One practical answer I use in my own portfolios is to create a “covered-call sleeve” built around low-cost Vanguard ETFs. In this article I’ll walk you through a repeatable, tax-aware approach: which Vanguard ETFs I prefer as the underlying, how to size the sleeve, how to structure monthly covered-call sales, and...

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I often get asked by small multifamily owners: How many months of rent reserves should I keep, and where should I park that cash? It’s one of the most practical risk-management questions in real estate, and the short answer is: it depends. But that’s not very satisfying, so below I walk through the factors I use to set reserve levels, present pragmatic reserve targets for different risk profiles, and explain where to hold the money so it’s...

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I often get asked whether Vanguard target-date funds (TDFs) can double as a taxable retirement glidepath — that is, whether you can hold a Vanguard TDF in a taxable account and simply use it as the default sequence of withdrawals during retirement. The short answer is: yes, you can, but the tax consequences and practical implications mean you should approach this deliberately rather than by default. In this piece I walk through the tax...

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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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I often approach equipment decisions the way I evaluate an investment: weighing risk, expected return, and fit with my objectives. Selecting a padel racket is exactly the same kind of trade-off. Over the years I've test-driven many models from Bullpadel, Nox, Head, Adidas, Wilson, Siux, and Babolat, and I use that hands-on experience combined with a data-minded approach to help you choose the racket that will give you the best performance per...

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I’ve been combining dividend investing with covered-call overlays for years to extract incremental income while keeping downside risk in check. When done carefully, a covered-call “income sleeve” can boost cash returns for a dividend-focused portfolio—but tax treatment can quietly erode those gains if you don’t structure it correctly. Below I walk through a pragmatic, data-driven way to build a tax-efficient covered-call sleeve that...

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I’ve spent years watching REITs move from steady dividend machines to distressed assets — and often the warning signs were sitting in the financials long before the market’s price action screamed “sell.” If you want to spot trouble early, you need to look past the headline dividend yield and dig into a handful of ratios and metrics that reveal credit strain, cash-flow weakness, and operational stress. Below I walk through the...

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