17 Financial Decisions Every Family Faces When Relocating to Costa Rica

Decision 1: Are you moving permanently or just trying it out?

This single decision changes everything downstream: what you do with your house, how you handle investments, which visa you need, and your entire tax strategy.

Options:Going for good (sell house, restructure investments, commit to residency visa) | Trying it for 1-3 years (keep house, keep accounts, use tourist or rentista visa) | Haven't decided yet. Drifting without an explicit decision means building on the wrong financial structure.

Decision 2: Can you actually afford this?

Two parts: what does your life cost there, and where is the income coming from? You need reliable income — pension, Social Security, remote work, or investment distributions. Savings alone burn down.

Key figures: Comfortable couple in the Central Valley: $3,000-$3,500/month. Elevated lifestyle: $4,000-$5,000. $500K+ net worth means a smooth transition. $150K is the bare minimum. Below $150K, the margin for error is razor thin. You cannot legally work in Costa Rica until you have permanent residency (3+ years).

Decision 3: What's your exit plan if it doesn't work out?

If you sold the house, where do you live when you come back? If you restructured investments, can you undo it? Having an exit plan actually makes you more likely to go — it removes the catastrophic downside and lets you commit with confidence.

Decision 4: Is your whole family actually on board?

The number one reason expat moves fail is not money — it is one person being more committed than the other. If one spouse is all-in and the other is going along to keep the peace, that is a time bomb. Kids add another layer depending on age.

Decision 5: What do you do with your brokerage accounts?

Your US brokerage account does not automatically close when you move, but it may get restricted. If you end up in the wrong type of fund, the IRS has a special penalty waiting.

PFIC trap: If you hold foreign-domiciled funds, the IRS taxes gains at the highest marginal rate PLUS backward-compounding interest. The effective tax rate can exceed 50%. Restructure accounts BEFORE your address changes — this requires 4-6 weeks minimum lead time.

Decision 6: What are you doing with the house and the business?

The sell-vs-rent decision on your house is one of the biggest financial forks of the whole move.

Key facts: A house sale can take 100+ days from listing to closing. Capital gains exclusion: $250K single / $500K married filing jointly. If your home has appreciated above the exclusion, timing sales across tax years matters. If you own a business, map the unwind or remote-operations plan months before you leave.

Decision 7: What changes with your taxes when you leave?

You still file US taxes. Forever. That is citizenship-based taxation. Costa Rica runs a territorial tax system — you only pay taxes on income earned in Costa Rica.

Decision 8: Which visa do you actually need?

Your visa type determines tax obligations, healthcare access, and whether you need to buy property.

Decision 9: Are you renting or buying in Costa Rica?

Most expats rent for the first 6-12 months. If you are going inversionista visa, you need to buy — and buying triggers a reporting requirement most people miss.

Decision 10: What happens to your Medicare?

Medicare does not cover you outside the US. But dropping it creates a permanent penalty that follows you for life.

Decision 11: What's your healthcare plan for day one?

US coverage ends the day you leave. Costa Rica's public system (CAJA) requires residency. Residency takes 10-24 months to process. That is a healthcare canyon, not a gap.

Solution: Private international insurance bridges the gap immediately. After residency, most expats run a dual system: CAJA (~$65/month) for major care plus a private plan for speed — about $350/month for a couple.

Decision 12: Which of your insurance policies still work abroad?

Many US insurance policies have foreign residence clauses that void coverage when you move. Auto insurance does not transfer. Homeowner's policies may have location requirements. Even life insurance can have foreign residence exclusions. Audit every active policy at least 60 days before moving. Auto insurance in Costa Rica requires a separate policy through INS (the national insurer).

Decision 13: Is your estate plan still valid when you move?

Your US estate plan — will, trust, power of attorney — has no legal authority in Costa Rica. If you have assets in both countries, your family could face two separate legal systems with no coordination. Cross-border estate planning that covers both jurisdictions is a protection decision, not a nice-to-have.

Decision 14: Where in Costa Rica are you going?

Community is a basic human need — and the hardest thing to build abroad. Your YouTube dream town might not be your daily-life town.

Options: Central Valley (best infrastructure, international schools, spring-like climate) | Pacific Coast (lifestyle-first, tourist pricing) | Caribbean Coast (laid-back, cheaper, fewer services) | Mountains/Rural (cooler, isolated, lower cost) | Intentional communities (built-in community from day one). Visit first. Rent 3-6 months before buying.

Decision 15: Do you know what a normal Tuesday actually looks like?

The gap between vacation Costa Rica and daily-life Costa Rica is enormous. The feria feeds a family for $11. Maxi Pali for basics. AutoMercado is priced like Whole Foods. PriceSmart is Costa Rica's Costco. Importing a car can double its price. Opening a bank account does not require residency, but takes more steps without it.

Decision 16: What about schools?

School availability may determine your location more than any other factor. International schools cluster in the Central Valley. Outside it, options shrink fast. Private schools run $5,000-$15,000/year — a significant budget item most people underestimate. If you have kids, research schools first, then pick your neighborhood.

Decision 17: Can you actually get all of this done in 90 days?

All 16 previous decisions connect to each other. They all have deadlines. Most need to happen before you get on the plane.

The 90-day sequence: Month 1 — lock go/no-go decisions, start investment repositioning, begin visa application. Month 2 — list or rent the house, sequence capital gains, secure healthcare bridge, enroll schools. Month 3 — map compliance calendar, restructure accounts, activate bridge policy, fly. Every step has dependencies. Miss one and the rest shift.