In this episode of Expat on a Budget, I sit down with international tax lawyer and long-time expat Bobby Casey, who’s built a life across multiple countries. We start with how a “test run” abroad led him from Estonia to Latvia, and how he now rotates between home bases in Mexico, Latvia, and the U.S.
But the heart of this conversation is U.S. healthcare—and why it’s a major factor in why so many Americans consider leaving. Bobby breaks down what most people misunderstand about medical bills, insurance, payment plans, and how hospitals bill (and negotiate). We also talk about getting care abroad, when he would return to the U.S. for treatment, and how to think about healthcare as part of a broader “live anywhere” strategy.
If you’re even quietly considering a move abroad—especially if healthcare costs are part of the equation—this episode will give you a new lens on what’s possible.
In this episode, we cover:
Why US healthcare costs are a top reason Americans consider leaving the US
How hospital billing works (and what most people misunderstand about medical bills)
The reality of living without US health insurance—and what that does and doesn’t mean
Negotiating medical bills and how payment plans can change the outcome
When it can make sense to get care outside the US (and when you might still return)
How “medical tourism” fits into an expat plan for routine and elective procedures
The mindset shift from “moving abroad once” to building multiple home bases
A quick look at residency abroad (Mexico/Europe) and why some places are easier than others
The practical planning layer: healthcare + residency + lifestyle design working together
If you’re in the US (or anywhere) doing the math—healthcare, housing, day-to-day costs—and wondering whether there’s a smarter way to build a life with more stability and choices, this episode will help you see the options more clearly. It’s practical, honest, and focused on what you can actually do next—whether you’re ready to move or just starting to explore.
Find Bobby Casey’s Digital Services for Nomads Here
⏱ TIMESTAMPED HIGHLIGHTS:
00:00:17 — Riga, Latvia was the place they really liked.
00:00:22 — Estonia was meant to be a one-year “test run” abroad.
00:00:34 — They returned to North Carolina with the plan to sell everything.
00:00:44 — After liquidating, they moved back to Latvia (how Latvia happened).
00:02:25 — Bobby explains who he helps: location-independent entrepreneurs/freelancers abroad.
00:03:30 — His company (BusinessAnywhere) handles formation, banking, mailbox, bookkeeping, filings, etc.
00:04:19 — He’s based in Playa del Carmen, Mexico (winter home).
00:05:13 — His three home bases: Mexico, Latvia, and North Carolina.
00:11:13 — US citizens have citizenship-based taxation: tax residency no matter where they live.
00:14:35 — Residency difference: Latin America often just wants proof of funds; Europe usually requires a specific reason.
You can also find a video of this podcast on YouTube if you’d rather watch there 😃
Ready to Plan Your Own Move?
My goal is to help you make your dream of moving abroad a reality. Here are a few ways I can help:
Personalized Consulting: I offer à la carte Consultations, an asynchronous Async option for busy schedules, and comprehensive Packages.
Online Class: Learn my entire framework in my “How to Move Abroad” course, designed to take you from start to dream destination.
Free Resources: If you’re just starting, check out my free “How to Live Abroad” series.
I also have some amazing offers from International Living that may interest you!
If you’re specifically interested in moving to Portugal, this is a great resource: Portugal Made Easy
There’s also a wonderful guide to help you Live Better Overseas
And this!!! How to Move out of the US
My Expat Toolkit (The Tools I Use & Trust)
Banking & Money:
Wise: For transferring money internationally. Use my referral code for a fee-free transfer up to $600.
Charles Schwab: The best bank account for expats. No foreign transaction fees and unlimited ATM fee rebates worldwide.
Chase Sapphire Preferred: My go-to credit card for travel hacking and earning points, with no foreign transaction fees.
Travel & Connectivity:
ExpressVPN: The VPN I use to keep my connection secure. Get three extra months with my link.
eSim Nomad: The most reliable eSIM I’ve found for staying connected on the go.
Home Exchanges:
Kindred: The home exchange platform I used to stay in a gorgeous L.A. bungalow for three weeks.
HomeExchange: The world's leading home exchange platform, connecting over 200,000 members across 155 countries for reciprocal or points-based home swaps.
**Some of the links above are affiliate links, which means I may earn a small commission if you choose to use them—at no additional cost to you. You’re under no obligation to use these links.
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