Year End Checklist for Your Money, Taxes, Points and Miles

#92: Chris shares his list of the top year end optimizations to consider for your taxes, money, points and miles. That includes tax-loss harvesting, charitable deductions, retirement contributions and FSA/HSAs. It'll also cover taking advantage of all your annual credit card credits and perks.

Partner Deals (Advertiser Disclosure)

Masterworks: VIP access to skip the waitlist

Pacaso: Free early access to listings and $2,500+ in closing credits

Rocket Money: Easily cancel your unused subscriptions

Athletic Greens: Free 1 year supply of Vitamin D and 5 free travel packs

Daffy: Free $25 to give to the charity of your choice

Selected Links From The Episode

Taxes/Investing

• Gelt: Tax planning service (skip the waitlist!)
• Gelt Tax Guide: Tax Concepts Worth Knowing During a Recession
• All the Hacks Newsletter: All About Investing Part 2
• Donor-Advised Fund Definition
  • Daffy: $25 to towards a charity of your choice
• Tax-Loss Harvesting
• Wash-Sale Rule
• Series I Savings Bonds
• Opportunity Zone Investing
• Wealthfront: $5,000 managed free
• Grail test: Detect Cancer Early
• Augusta Rule: Tax Rules for Renting out Your Home

Points/Miles/Credits

• FlyerTalk: Example Forum Page for Southwest Credits
• The Platinum Card® from American Express: $200 Airline Credit | $200 Prepaid Hotels | $200 Dell | $50 Saks | $15/mo Uber ($35 in Dec) | $20/mo Digital Entertainment
  • Saks Credit Ideas: Aesop and Mack Weldon Underwear
• American Express® Gold Card: $10/mo Dining | $10/mo Uber
• Chase Sapphire Reserve®: $300 Travel | $5/mo DoorDash | $10/mo Gopuff
• Capital One® Venture X Rewards Credit Card:: $300 Travel
• Hilton Honors American Express Aspire Card: $250 Resort Credit | $250 Airline Credit | Annual Free Night | Complimentary Diamond Status | 150,000 point signup bonus

Full Show Notes

Introduction to this week’s episode (00:00)

Should you take the standard deduction or should you itemize? (1:25)

Accelerating or deferring income (3:59)

Charitable donations (4:56)

Donating appreciated assets (5:37)

Donor-advised fund (7:28)

Tax-loss harvesting and common index fund pairing (8:39)

Selling crypto at a loss/abandonment loss (10:57)

Opportunity zone investing (14:40)

I-Savings Bonds (15:17)

Stock options/ISOs (16:45)  

Retirement accounts (17:37)

Contributing to a 529 account (19:38)

Use up the money in your FSA account (20:37)

Max out your HSA account (21:31)

Energy efficiency upgrades (22:11)

EV tax credit (23:12)

Hired as a business vs a W-2 employee (23:27)

Business owner tax optimizations (24:52)

HSA/FSAs and the Augusta Rule (30:19)

California municipal bonds (32:31)

End-of-the-year housekeeping: points and miles (32:54)

Chasing flight and hotel status (34:05)

Taking advantage of benefits/upgrades/lounge access passes (35:14)

Hotel, credit card, and airline credits (35:39)

Credit card: travel credits (38:42)

Benefits included with the American Express Hilton Aspire card (39:18)

San Francisco event (40:47)

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Rocket Money

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(see important disclosures at masterworks.io/cd)

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Editor’s Note: Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.