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The Boring Newsletter, 8/17/2025

Charity care and other strategies to reduce medical bills, and organizing paperwork for bills you do have to pay Hi Friendos, Last week I promised to discuss practical considerations for using FSAs and HSAs, and tracking medical expenses in general. Before I get to that, I want to talk about steps you can take to […]

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The Boring Newsletter, 8/9/2025

For tax purposes, a “Qualified Medical Expense” is mostly what you think, plus a bit more Being an adult in the U.S. means sometimes dealing with things that are both dull and important, like taxes and medical insurance. Today I focus on the intersection of these: what constitutes a “qualified medical expense” for tax purposes. […]

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The Boring Newsletter, 1/18/2025

Hi Friendos, Today I am tackling a topic that lives up to this newsletter’s “boring” moniker: recordkeeping. If you have federal student loans and are on income-driven repayment, please read this TODAY before the new administration takes office. First, a personal anecdote that illustrates the importance of good recordkeeping. A couple months ago my spouse […]

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The Boring Newsletter, 10/29/2023 🩺

Hi Friendos, Today is our fourth installment discussing tax-advantaged medical accounts (HSAs and FSAs) where we’ll look at how these fit into the overall selection of a health insurance plan. I am always grateful to have insurance (really grateful) but I *hate* that choosing a plan is so complicated. My approach is to consider the […]

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The Boring Newsletter, 10/15/2023

Hi Friendos, Last week I wrote about how FSAs and HSAs save you money (lowering your taxes), and I promised to talk this week about how much they can save you, so you can decide if putting your $ in one is worth it to you. This week is a deep dive on FSAs. Next […]

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The Boring Newsletter, 10/8/2023

Hi Friendos, Health insurance open enrollment is coming up in a few weeks so this month I’ll write about some related topics. This week is about explaining the financial benefit from FSAs and HSAs (“flexible spending account,” “health savings account”), specifically, how they save you money. Next week I’ll talk about how much. This helps […]