The Problem. The Opportunity. The Solution.
Most expats fail because their strategy is warped by misinformation. We provide the operational discipline to ensure your success.
The Problem:
The "Gringo Tax"
Overpaying for rent, visas, and local services due to a lack of objective intelligence.
The Opportunity: Strategic Leverage
Your income goes further here. We show you how to maintain a Top 5% lifestyle on a fixed budget.
The Solution: Operational Discipline
Our military-grade blueprint ensures a smooth, cost-effective transition into the DR.
Start Your Island Journey the Right Way
Consultations
Stop Guessing. Start Planning.
Moving to the Dominican Republic is a major life change. One wrong decision on an apartment or legal process can cost you thousands. Book a 1-on-1 consultation with Jerry and Sheila. We provide the "Veteran Strategy" and "Local Insight" you need to navigate your move safely and efficiently.
The Airbnbs
Stay Safe. Stay With Us.
Experience Santo Domingo Este with peace of mind. We offer two fully furnished, secure Airbnb units hosted personally by us. Enjoy the comfort of a modern home with the added security of having a US Veteran and local expert nearby. Perfect for scouting trips or island vacations.
A real conversation many expats avoid, but shouldn’t.
💭 Stop leaving money on the table. If you are a Veteran living abroad or planning to move, here is exactly how to access your $3,700/month VA Disability benefits
Digital Products & Merch
The Island Reset Toolkit & Gear
Get the tools you need and the look you want.
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Essential Guides: Download our "Moving to DR Checklist" and "Budget Guides" to fast-track your planning.
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Official Gear: Rep the "Island Living" brand with our exclusive t-shirts, mugs, and accessories.
Subscriptions
Join the Island Crew
Go deeper than the vlog. This is our private community for the real conversation. Members get unfiltered advice, direct Q&A access to Jerry & Sheila, and real-time updates on our business and life in the DR that we don't share publicly.