End of Year Checklist for Your Taxes, Points and Miles

There are real dollars on the line before December thirty‑one, so I’m walking you through a simple year‑end checklist for taxes, money moves, and your points and miles. I’ll turn it into a downloadable PDF at allthehacks.com/checklist, and quick reminder I’m not your tax advisor—if you want help, you can see the team I use at allthehacks.com/gelt.

Start by knowing whether you’ll itemize or take the standard deduction, then plan accordingly. With the SALT cap lifted to forty thousand dollars for many people under five hundred thousand dollars of income, bunching deductions can pay—prepay property taxes or a mortgage payment, stack charitable gifts, and consider appealing your property tax assessment; business owners may also use pass‑through entity tax elections in some states to sidestep SALT limits at the personal level.

Charitable giving is a powerful lever. Donating appreciated stock avoids capital gains and gives you a larger deduction, and a donor‑advised fund lets you give now for the write‑off and grant out later while the funds grow; that pairs nicely with bunching. One more twist: starting in twenty‑twenty‑six, itemizers lose the first half‑percent of AGI for charitable write‑offs, so twenty‑twenty‑five is an attractive year to load up gifts if you can.

A few new items this year: interest on qualifying new car loans can be deductible up to ten thousand dollars of interest for eligible vehicles, but it phases out as income rises. Make sure tips and overtime are coded correctly on your W‑2, and if you’re sixty‑five or older there’s a new above‑the‑line deduction with income limits; if you’re near a threshold, consider shifting income or adding pre‑tax contributions to stay eligible. Also, moving into a higher bracket only affects dollars above that line, not all your income.

On investing, look for tax‑loss harvesting before year‑end and avoid the wash‑sale rule by swapping into similar, not identical, funds; crypto currently isn’t covered by wash‑sale rules. If this is a low‑income year, you might even harvest gains at a zero capital gains rate; specialized strategies like opportunity zones or solar deals exist, but talk to a pro.

Max retirement accounts while you can. Employee 401(k) deferrals must hit payroll by December thirty‑one, and plans that allow a mega backdoor Roth can be huge. IRA and Roth IRA contributions generally run until mid‑April, but it’s simpler to fund now; if you’re blocked from a Roth, the backdoor Roth works if you manage the pro‑rata rule, often by rolling pre‑tax IRA money into a 401(k). Low‑income years are also prime for Roth conversions, and if you hold ISOs, you may be able to exercise up to your AMT edge with a CPA’s help.

Use your FSA before it disappears—book care, refill prescriptions, or buy eligible items, and donate extras rather than waste them; if you’re leaving a job early next year, timing big procedures can be smart. HSAs are triple tax‑advantaged, so max them if you’re on a qualifying plan, invest the money, and pay current bills out of pocket while saving receipts to reimburse yourself later tax‑free.

Home upgrades can still earn incentives. Many efficiency improvements have annual caps that require the work to be in service by year‑end, and solar generally qualifies for about thirty percent of the installed cost; if it was already on your list, try to get it done.

For kids and gifting, 529 plans may offer state tax breaks, can cover some K‑12 costs, and unused funds can roll to a Roth IRA for the beneficiary up to thirty‑five thousand dollars after fifteen years. You can also use the annual gift tax exclusion—nineteen thousand dollars per giver per recipient—and even five‑year superfund a 529 if that fits your plan.

Status chasers, this is your last window. If you’re a hair short, a quick mileage or mattress run can push you over the line—hotelmattressrun.com helps find cheap elite nights—and some programs let credit‑card spend count as qualifying activity that must post by year‑end; Hyatt business spend resets at ten‑thousand‑dollar blocks, and don’t forget to select your milestone choice benefits before they expire.

Before the calendar flips, watch annual earning caps and spend‑triggered perks on your cards, and use your calendar‑year credits; the CardPointers app is great for tracking without linking bank logins. You can often double or even triple‑dip by opening late in the year and spanning multiple calendar cycles—for example, Amex Platinum airline incidentals and Fine Hotels and Resorts credits, Amex Gold’s Resy credits, Hilton Aspire’s resort and quarterly flight credits, Bank of America Premium Rewards Elite airline and lifestyle credits, Chase EDIT and dining or event credits, select Ritz and Hyatt Business calendar‑year credits, Citi Strata Elite hotel and splurge credits, and various American Airlines co‑brand perks; some issuers, like Capital One and U.S. Bank on certain cards, run on cardmember‑year timing instead.

Close the loop with a quick audit. Check airline and hotel accounts for point expirations and nudge activity if needed, and put a small charge on any dormant credit card so it stays open. The full checklist is at allthehacks.com/checklist—share it with a friend if it helps—and if you want more of this, hit follow. We’re taking a short holiday break and will be back on the thirty‑first; you can always reach me at [email protected].