Navigating Expat Taxes: Insights for Dream Retirees

Snagged a dream place in Puerto Vallarta or Mykonos… and now the IRS is at the door? Today we’re joined by expat tax expert Michelle Miele (Director of Paperwork) to decode how U.S. taxes work when you retire abroad. We cover Social Security, IRA/401(k)/Roth distributions, self-employment/online business income, countries with and without U.S. tax treaties, foreign tax credits, and common traps (like selling your U.S. home after you change tax residency). Three real-world scenarios—Mexico, Portugal, and Thailand—show you how this plays out.

Key Takeaways:

Filing ≠ owing. You’ll likely file in the U.S. even after moving, but credits/treaties can prevent double tax.
Order matters: generally file where you live first, then the U.S., and use foreign tax credits to offset.
Roth alert: some countries tax Roth distributions; plan timing and residency to protect withdrawals.
Entity traps: your LLC/S-corp may be treated as a corporation abroad; confirm local treatment before you move.
Real estate timing: if selling a U.S. primary home, sell while still a U.S. tax resident to preserve exclusions.
Benefits trade-off: higher taxes in some countries may be offset by much lower healthcare and living costs.

Related Queer Money Episodes:

Ep 614 — Top 5 Cities for Gay Retirement in Taiwan
Ep 610 — Best LGBTQ+ Retirement Cities in Greece
Ep 607 — The $6,000 “Boomer Bonus” Deduction Strategies
Ep 599 — Affordable Gay-Friendly Cities in Portugal
Ep 542 — Gay Expats in Mexico: Pacific Coast Edition

Chapters:

00:11 - Navigating Taxes as an Expat Retiree
03:51 - Understanding Tax Obligations for Expats
11:34 - Tax Implications of Living Abroad
14:10 - Tax Obligations for Expats: A Case Study
21:25 - Retirement Abroad: Tax Implications
28:09 - Planning for Retirement Abroad

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