How to compare municipal bonds, treasury bills, and money market funds for idle portfolio cash in taxable accounts

I track dozens of local markets each year, not because I enjoy scrolling listings, but because the places that re-rate fastest are almost always those where housing supply shifted before the narrative caught up. A supply shock — whether it’s a sudden halt to new construction, a municipal zoning change, or a landlord exodus that trims rental stock — can create a window where prices rise faster than the broader market. Below I share a...

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I’ve often been asked by investors who hold a concentrated position in a single stock: “How can I generate current income from this position without selling a lot of shares and triggering a big tax bill?” Over the years I’ve used a compact, repeatable framework that combines covered calls with selective, partial tax-loss harvesting to create an income sleeve around a concentrated holding. It’s designed to be simple, tax-aware, and...

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I’ve been asked repeatedly whether a covered-call sleeve on SPY can stand in for dividend income for retirees without sacrificing long-term growth. It’s a practical question: retirees want reliable cash flow, lower volatility, and continued upside to keep up with inflation. I’ve tested the idea from both a theoretical and empirical standpoint — blending option mechanics, historical SPY data, and portfolio-level thinking — and here’s...

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I remember the morning a close friend called me after a small-town headline announced a local lottery winner. We talked about the immediate joys — plans, relief, and the impulse to partager ses gains au loto avec ses proches. That impulse is powerful and natural. But as someone who writes about personal finance, I also know that generosity without a plan can create tax complications, family friction, or even legal headaches. In this article I...

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I often get asked a version of the same question by rental owners: “Should I refinance my rental to a shorter term to improve cash flow?” At first that sounds counterintuitive — shorter terms usually mean higher monthly payments — but the right combination of existing loan structure, interest-rate movement, and closing costs can make a shorter-term refi the smart move. Below I walk you through a numbers-first case study and a simple...

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When I underwrite brownfield conversions, the single most common question I get is: how much of a cap rate haircut should I apply to account for environmental remediation risk? There isn’t a one-size-fits-all answer, but over years of working with investors, redevelopment teams, and environmental consultants I’ve developed a pragmatic framework that converts uncertainty into defensible, repeatable adjustments to valuation.Why a cap rate...

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I often get asked how to reduce lifetime “tax drag” — the cumulative hit that taxes impose on investment returns — without sacrificing flexibility. One elegant, underused approach is a taxable-to-IRA Roth conversion ladder built around tax-efficient Vanguard funds. In this article I’ll walk you through how I’d construct this ladder, the practical mechanics, pitfalls to avoid, and example allocations so you can see how it works in the...

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When I first explored creative financing to scale multifamily acquisitions without giving up equity, I kept coming back to one idea: why not package reliable rental cash flows into a tradable note? A rent-backed note is exactly that—a credit instrument secured by future rental income rather than equity—and when structured well it can let sponsors raise capital, preserve ownership, and accelerate portfolio growth. Below I walk through how I...

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I often get asked by investors whether they should tap a HELOC or do a cash-out refinance to fund a rental purchase. Both tools unlock home equity, but they behave very differently for cash flow, taxes and portfolio construction. Below I walk through the trade-offs I use when advising clients and make the decision framework explicit so you can apply it to your own situation.Key differences at a glanceBefore diving into numbers and scenarios,...

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When I set out to replace an active small‑cap value sleeve in a taxable portfolio, my priority is straightforward: preserve the intended exposure to smaller companies that trade at value metrics while minimizing taxable friction and keeping costs low. Active small‑cap value managers can deliver compelling returns, but they often come with higher turnover and capital gains distributions that hurt taxable investors. In practice, the best...

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