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Plus: getting married in December, and paying your kid’s rent
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Good morning! Every Saturday, we open the mailbag, pour some strong coffee, and tackle the tax questions keeping America awake at 2 a.m.
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Here are this week’s topics:
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🚗 One missing detail can erase your entire mileage deduction.
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💍 It doesn’t matter when you got married this year — only that you did.
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🏠 Your kid moved out, but the IRS may still count him as living with you.
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Filing Made Simple
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🚗 The IRS doesn’t want your best guess. It wants a mileage log.
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I run my business as a sole proprietor and haven’t been tracking mileage carefully. What records does the IRS actually want to see?
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Good news: it’s not too late to start. Bad news: “I drive a lot for work” is not a record, it’s a vibe, and the IRS does not accept vibes.
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What the IRS wants in a mileage log
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Under IRS Publication 463, an “adequate” log needs five things for every business trip:
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The date of the trip
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Where you drove (a specific destination, not “downtown”)
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The business purpose — specific (“client meeting with Jane at Summit Financial,” not “work stuff”)
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The miles driven
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Your odometer reading at the start and end of the year
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Miss one of the five and the IRS has grounds to toss that trip — or your whole deduction, depending on how generous the auditor is feeling.
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Timing matters too. The records have to be contemporaneous, meaning logged at or near the time of the trip. A weekly log counts. Reconstructing 11 months of driving from memory next April does not, and it’s exactly the kind of thing that turns a routine review into a longer one.
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This year has an extra wrinkle. The standard mileage rate changed mid-year:
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That means the date on each trip isn’t a formality — it determines which rate applies. A log that just says “lots of driving, sometime this year” can’t do that math for you.
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Getting caught up
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Start tracking now with a phone app or a simple spreadsheet
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Go back through calendar invites, appointment records, and client emails to reconstruct what you reasonably can for the months you missed — noted honestly as reconstructed, not backdated as if you’d logged it that day
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Going forward, log weekly. It takes less time than your actual bookkeeping, which, coincidentally, is also something we can help with
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⚙️ THE TAXSTACHE TOOLKIT
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Find out if your log holds up — and what it’s worth in dollars — before the IRS does it for you.
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PRESENTED BY FINANCE BUZZ
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Earn up to a $250 travel bonus — no annual fee
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Pay 0% intro APR into 2027 while you earn toward your next trip. No annual fee, no catch. Just interest-free breathing room and a bonus waiting on the other side.
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Tax Strategies
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💍 Married by December 31? Congratulations, you’re married for the whole year.
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We’re getting married this December. Does it make more sense to file jointly for the whole year, or does timing matter?
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Congratulations! And no, timing doesn’t matter — at least not the way you’re picturing it.
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The IRS doesn’t prorate marriage. Your marital status on December 31 determines your filing status for the entire year, whether you said “I do” in January or 20 minutes before midnight on New Year’s Eve.
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There’s no split return, no “single for 11 months, married for one.” If you’re legally married by December 31, the IRS treats you as married for all 12, income you earned before the wedding included.
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So the real question isn’t “when” — it’s jointly vs. separately. For most couples, jointly wins. Joint filers generally get:
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A bigger standard deduction
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Better rates at most income levels
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Access to credits that filing separately either eliminates or shrinks — the Earned Income Tax Credit, education credits, and others
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Filing separately tends to make sense in narrower cases, like when:
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One spouse has heavy medical expenses tied to a lower individual income
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There’s an income-driven student loan repayment plan in the mix
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One spouse doesn’t want to be on the hook for the other’s tax liability
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Run the numbers both ways before you file, especially in year one. Tax software makes this fast, and the difference is rarely dramatic, but it’s worth the 10 minutes.
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One thing timing does affect: your withholding. Getting married midyear without updating your W-4 is how couples end up owing more than expected the following April — two single filers’ worth of withholding doesn’t automatically add up to what a joint return needs. Update your W-4 once the wedding’s behind you, not in March when you’re staring at a balance due.
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⚙️ THE TAXSTACHE TOOLKIT
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One tax return. One shot at getting it right the first year. Don’t guess.
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Every Thursday, we go to work.
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The TaxStache Business Edition breaks down the tax and finance topics that actually matter to business owners, from quick intros to in-depth dives. Plus book, podcast, and video recs to keep you sharp, and a weekly download you can put to use right away.
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If you own a business (or you’re building one), this one’s for you.
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Would you like to receive our Thursday Business Edition?
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Filing Made Simple
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🏠 Paying your son’s rent while he’s in school still counts as support — for you.
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We’re helping pay our son’s rent while he’s in school. Does that count as support for dependent purposes?
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Yes, and it works in your favor twice over — once on residency, once on support.
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Residency, first, since it trips people up. To claim him as a dependent, he generally has to live with you for more than half the year. Sounds like a problem if he’s in a dorm or an apartment near campus for nine months. It isn’t — the IRS treats time away at school as a temporary absence, not a break in residency, the same way it treats military service or a hospital stay. As far as the dependent test is concerned, he’s still living at home.
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Residency’s the easy part. The support math is where families actually get tripped up.
👉 Check the Support Test
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Then there’s the support test — and this is where paying his rent actually helps. For a “qualifying child” (which he likely is, if he’s under 24 and a full-time student for at least five months of the year), the test isn’t how much support you provided — it’s whether he provided more than half of his own.
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A few things worth knowing:
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Every dollar you spend on his rent, food, and other living expenses is a dollar he didn’t have to earn or borrow himself — that makes it easier for him to clear the bar, not harder
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A part-time job or financial aid doesn’t disqualify him, as long as he isn’t covering more than half of his own total support himself
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Scholarships don’t count against him either way — the IRS excludes them from the calculation entirely
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Keep a rough tally of what you’re paying — rent, groceries, health insurance, tuition not covered by scholarship — versus what he’s earning and spending on himself. It doesn’t need to be forensic-grade, but if the numbers are close, you’ll want to know before the IRS asks.
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⚙️ THE TAXSTACHE TOOLKIT
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The IRS doesn’t take your word for it. Run the actual numbers before you claim him.
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