All the Hacks: Money, Points & Life

Episode: "End of Year Checklist for Your Taxes, Points and Miles"

Host: Chris Hutchins
Date: December 10, 2025

Overview

In this solo episode, Chris Hutchins delivers an actionable, plain-English, end-of-year money and travel checklist designed to help listeners maximize savings, hack their taxes, optimize points/miles, and not leave any value on the table. He covers tactical moves across 10 tax topics, changes for 2025 and 2026, and digs into credit cards, points, and miles strategies, including annual deadlines and status tips.

Listeners are promised a downloadable, comprehensive checklist at allthehacks.com/checklist.

Key Discussion Points & Insights

1. Understanding Standard vs. Itemized Deductions

• Timestamps: 00:00–05:00
  • Standard deduction for 2025:
    • Single: $15,750
    • Married Filing Jointly: $31,500
    • Head of Household: $23,625
  • Importance of evaluating whether to take standard or itemize.
  • "The goal here is not to wait till the end of the year and find out what happened. The goal is to try to benchmark where you're going to end up..." (A, 01:45)

Bunching Deductions:

• Consider grouping (bunching) deductions in one year (prepay property taxes, make large charitable contributions) to exceed the standard deduction, then take the standard deduction in low-deduction years.

2. SALT Limit (State and Local Tax Deduction) Changes

• Timestamps: 05:00–08:00

  • 2025 law: SALT cap increased from $10,000 to $40,000 for income under $500,000.

  • Prepaying property tax and mortgage payments can help max out new SALT cap.

  • For business owners: Pass-through entity tax workaround can maximize deductions.

    "If in scenarios past, you were stuck at never being able to itemize and it never made sense, now that might actually make sense, especially when you add in your mortgage interest, any charitable contributions, and those kinds of things." (A, 06:30)

3. Charitable Giving: Cash, Noncash, and Appreciated Asset Donations

• Timestamps: 08:00–14:17
  • Itemizing is required to deduct charitable donations in 2025.
  • Donate appreciated assets (stocks or crypto held >1 year) to avoid capital gains tax and maximize deduction.

    "If you have any types of securities or assets that have appreciated in value, donating those assets to charity is always going to be a more effective strategy than just donating cash." (A, 11:40)

  • No wash-sale rule for donating appreciated securities; rebuy immediately if desired.

Donor-Advised Funds (DAF):

• DAFs like Daffy simplify bulk donations and allow strategic “bunching.”
• DAF contributions now could lock in deduction before 2026 rules change.

Upcoming Changes:

• In 2026, a 0.5% AGI floor for itemized charitable deductions will apply.

  "2025 is a fantastic year if you're already itemizing to contribute to a donor advised fund..." (A, 14:17)

4. New 2025 Tax Changes

• Timestamps: 14:17–19:20

  • Car loan interest deduction (up to $10,000 interest/year) for certain new US-assembled cars with income limits (phased out above $150k single/$250k married).

  • Deductions for qualified tips and overtime income (check W-2 coding).

  • New senior deduction: $6,000 single / $12,000 married, with income phase-outs.

    "If you're in the right income threshold, this is really interesting ... trying to make sure that you fall into the right thresholds for these income caps." (A, 17:45)

5. Shifting Income and Strategic Tax Brackets

• Timestamps: 19:20–21:30
  • Use strategies (401(k), HSA contributions) to keep taxable income under key thresholds to qualify for deductions/credits.
  • Reminds listeners marginal rates only apply to income above the threshold.

6. Capital Gains, Tax Loss Harvesting, and Investment Optimization

• Timestamps: 21:30–28:10
  • Tax loss harvesting: Sell losing positions to offset gains ($3,000 can offset income; excess carries forward).

    "Short term losses... are even more valuable because they also can offset short term gains which are taxed at much higher rates than long term capital gains." (A, 22:50)

  • Be careful with wash-sale rule—buy similar, not identical securities.
  • No wash-sale rule on crypto: can sell and rebuy to realize losses.
  • In low-income years, consider realizing gains up to 0% capital gains tax bracket.

7. Retirement Accounts: Maximize Before Year-End

• Timestamps: 29:30–37:50
  • 401(k) employee contribution 2025 limit: $23,500 (+$7,500 catch-up 50+). Must be contributed by 12/31, via payroll.
  • Mega Backdoor Roth: Use after-tax contributions and in-plan conversion if your employer allows, up to $69,000 total.
  • IRA & Roth IRA contribution limit: $7,000 (+$1,000 catch-up). 2025 contributions allowed until April 15, 2026 (account should be opened by year-end).

    “If you have the money to do an IRA contribution and you want to, I would encourage you to do that before December 31st. To make things more simple...” (A, 29:58)

  • Backdoor Roth: Make non-deductible contribution to traditional IRA, then convert to Roth IRA (“pro rata rule” complications if you have large pre-tax IRA balances).
  • Roth conversions: advantageous in low-income years.
  • ISOs (stock options): Be careful to avoid triggering AMT—work with a CPA.

8. Tax-Advantaged Health Accounts (FSA & HSA)

• Timestamps: 37:50–44:30
  • FSAs are use-it-or-lose-it (some rollover). Buy medical supplies or donate eligible goods to avoid leaving money unspent.
  • Tip: Max FSA before a planned job change and spend early to “arbitrage” the system.
  • HSAs for those on high-deductible plans (2025): $4,300 individual / $8,550 family.
    • Triple tax advantage: deductible in, grows tax-free, withdrawals tax-free for medical.
    • “Let that money grow tax free as long as possible and pay my medical expenses out of pocket...”
    • Save medical receipts for future reimbursement.
  • Can contribute to IRAs and HSAs until April 15 the following year, but best to plan by 12/31.

9. Home Energy Upgrades & Credits

• Timestamps: 44:30–45:50
  • 2025 is the last year for certain energy efficiency improvements ($3,200/yr on windows, doors, etc.).
  • Solar credit: 30% of install cost, must be in service by 12/31/2025.

10. Kids, Education Savings and Gift Exclusions

• Timestamps: 45:50–49:00
  • 529 plans: State tax benefits + tax-free growth for education; act before 12/31 for state deduction.
    • New: Up to $35k in unused funds can roll to Roth IRA after 15 years.
  • 2025–26 births get an extra $1k in new "Trump accounts" (launch July 4, 2026; details pending).
  • Gifting: $19,000 per person/per giver; can superfund 529s with up to 5 years at once.
  • Kids with earned income can contribute to Roth IRA; hiring your kids in the family business is an effective, tax-advantaged move.

11. Self-Employed & Small Business Year End Moves

• Timestamps: 50:32–54:50
  • Issue 1099s, pay reasonable compensation (S corp).
  • Owner's health insurance deduction for S corps.
  • Solo 401k: Best-of-breed option for self-employed retirement (must be opened by year end).

    "The only other employee of your business can be your spouse. Otherwise you’re not eligible to contribute to your solo 401k..." (A, 51:25)

  • Bonus depreciation: Large equipment or vehicles can be fully depreciated in 2025.
  • Ensure all business expenses, home office deductions, are properly captured before 12/31.

Miles, Points & Credit Cards: End-of-Year Checklist

• Timestamps: 54:50–1:22:00

A. Status Chasing and Elite Requirements

• All airline/hotel status activities must generally be completed by 12/31.
• Mileage/mattress runs (often worth it if just one or two nights away from a major benefit).
  • "If you are one night away from hitting Hyatt Globalist ... find the cheapest possible night before the end of the year and go book a night." (A, 55:58)
• Credit card spend can earn extra elite nights/points/dollars—make sure charges post in time.

B. Selecting Choice Benefits

• Many programs require you to pick milestone/choice benefits earned by year-end; don't let these lapse.

C. Maximizing Card Spending Bonuses Before Reset

• Many cards have annual cap for elevated spend rewards (e.g., Amex Gold, Amex Blue Biz Plus, BOA Customized Cash).
• Hit spend milestones for free night certificates (e.g., Hilton, Hyatt, Marriott).

D. Annual Credits & Perks: Use Them or Lose Them

• Amex:
  • Gold: $50 Resy credit—buy gift cards with Toast where possible.
  • Platinum: $200 airline fee, $100 Resy, $50 Saks, $75 Lululemon, $200 Oura Ring, CLEAR, Equinox, Soul Cycle, $300 FHR hotels.
  • Amex Hilton: $200 resort, $50/quarter flight, CLEAR.
  • Delta Amex: Up to $250 Delta Stays hotel credit.
• Bank of America:
  • $300 airline (Elite), $150 lifestyle.
• Chase:
  • $250 EDIT (hotel collection), $150 restaurant (Sapphire Tables), $150 StubHub, $200 Google Workspace, $50 giftcards.com, $200 ZipRecruiter, etc.
• Citi:
  • $300 hotel (Strata Elite), $200 splurge, $100 hotel (Strata Premier), $250 travel (Prestige).
• American Airlines:
  • Turo credits, AVIS/Budget credits, Admirals Club passes, $100–$240 travel and inflight credits.
• US Bank Altitude Reserve:
  • $325 travel & dining credit based on cardmember year.
• Tip: Card Pointers app helps track all card credits—mark favorites to stay on top.

E. Points/Certificate Expiry and Account Housekeeping

• Check for miles/points that might expire; do a quick earning/redeeming activity to reset.
• Put a small spend on rarely used cards to keep accounts open (prevents issuer shutdown and protects credit score).

  "My longest running credit card was an old United card ... and Chase thought, well you haven't used it in three years, we're going to close it for you." (A, 1:21:08)

Notable Quotes & Memorable Moments

• On itemizing vs. standard deduction:

  "The goal here is not to wait till the end of the year and find out what happened. The goal is to try to benchmark where you're going to end up..."
  (A, 01:45)

• On donor-advised funds:

  "If you have any types of securities or assets that have appreciated in value, donating those assets to charity is always going to be a more effective strategy than just donating cash."
  (A, 11:40)

• On maximizing business deductions:

  "If you have consulting revenue, if you sell art, all kinds of things that could count as business income."
  (A, 50:35)

• On annual credit urgency:

  "The only other thing that I like to do at the end of the year is just run through all my airlines, my hotels and my credit cards ... make sure every card has at least one purchase from that year."
  (A, 1:21:08)

• Summing up the episode’s philosophy:

  "Never leave money on the table. This is your shortcut to upgrading your life, money and travel—all while spending less and saving more."
  (Opening, 00:00)

Quick-Reference Timestamps

• 00:00–05:00 — Standard vs. Itemized Deductions
• 05:00–08:00 — SALT Cap, Prepaying Taxes
• 08:00–14:17 — Charitable Donations, Donor-Advised Funds
• 14:17–19:20 — 2025 Tax Code Changes
• 19:20–21:30 — Income Shifting
• 21:30–28:10 — Investments, Tax Loss/Gain Harvesting
• 29:30–37:50 — Retirement Accounts, Mega Backdoor Roth
• 37:50–44:30 — FSAs and HSAs
• 44:30–45:50 — Home Energy Credits
• 45:50–49:00 — Kids, 529s, Gift Exclusions
• 50:32–54:50 — Business Owners’ Checklist
• 54:50–1:22:00 — Credit Cards, Points, Status, and End-of-Year Credits/Perks

Final Suggestions

Chris reiterates the power of systematic, strategic review before December 31st in tax, investments, credit card rewards, and status.
Checklist available at: allthehacks.com/checklist

For questions or feedback: podcast@allthehacks.com

No episode Dec 24 — back Dec 31 with year-end wrap-up.

Summary compiled based on full episode transcript and structured for clarity and easy action.