Welcome to Jerry & Sheila Island Living 🌴
I traded the U.S. grind for purpose, peace, and real estate in the Dominican Republic. After 21 years of service, I’ve shifted from the "rat race" to building a legacy. We provide the blueprint for your lifestyle redesign.
From navigating DR residency to managing profitable Airbnbs and growing a bilingual family, we share the unfiltered truth so you can move with confidence.
🚀 WHAT WE COVER:
Expat Relocation: Logistics, residency, and cost of living.
Real Estate & Investing: Turning a pension into wealth through DR property.
Bilingual Life: The raw reality of cross-cultural marriage.
Island Reset: The "Peace over Pressure" mindset.
📲 CONNECT WITH US:
🌐 Website: www.jerrysheilaislandliving.com (Guides & Consultations)
📸 Instagram: @jerrysheilaislandliving
📘 Facebook: @jerrysheila2023
New videos weekly. Subscribe to join the Island Crew.
#jerrysheilaislandliving #dominicanrepublic #expatlife #realestate #financialfreedom
Jerry & Sheila Island Living
When you think of "Island Living," what’s the actual goal?
1 day ago | [YT] | 10
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Jerry & Sheila Island Living
If you were getting out today, what’s your REAL plan?
3 days ago | [YT] | 5
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Jerry & Sheila Island Living
https://youtu.be/TxU99nvBuuY
You thought you had a plan after getting out… so did I.
Go to school. Use the GI Bill. Work part-time. Live at home.
Sounds solid, right?
That was my plan too, until I found myself struggling to make ends meet and eventually sleeping in my car.
Nobody talks about this part.
If you’re transitioning out of the military (or planning to), this video might save you years of setbacks.
🎥 Watch this before you ETS.
Let me know in the comments: what’s your exit plan?
3 days ago | [YT] | 35
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Jerry & Sheila Island Living
https://youtu.be/D9v6Z8-B4j8
We went so you don’t have to guess. 🇩🇴
Puerto Plata resort tour; real prices, real vibes, no sales pitch.
If you’re an expat, thinking about moving, or just visiting… this matters.
👉🏽 Watch it and decide for yourself: Is it worth it or nah?
#PuertoPlata #DominicanRepublic #ResortTour #ExpatLife #LivingInTheDR #MovingToTheDR #DRLife #TravelTruth #IslandLiving #JerryAndSheila #jerrysheilaislandliving #jerryandsheilaislandliving 🙏🏽👊🏽
5 days ago | [YT] | 60
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Jerry & Sheila Island Living
Quick clarity.
A lot of people have been asking to talk 1-on-1 lately… but don’t want to pay for it.
Here’s the line:
If you want personalized time, strategy, and real answers, that’s a paid consultation.
If not, the channel already has hundreds of hours of free game.
Both options exist. Choose what fits you.
www.jerrysheilaislandliving.com/book-online
1 week ago | [YT] | 82
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Jerry & Sheila Island Living
#expatlife #jerryandsheilaislandliving #jerrysheilaislandliving
1 week ago | [YT] | 74
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Jerry & Sheila Island Living
If you had $250k for a DR home, what would be your priority?
1 week ago | [YT] | 9
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Jerry & Sheila Island Living
Operation Legacy: How We Built Our DR Airbnb (And Avoided the Gringo Tax)
https://youtu.be/5d5yWkmhFbo
1 week ago | [YT] | 37
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Jerry & Sheila Island Living
What’s the BIGGEST thing stopping you from buying or investing in the DR?
👇 Vote honestly. Then watch the new video.
Most people don’t fail here from lack of money; they fail from hesitation.
#OperationLegacy #GroundIntel #DRRealEstate #VeteranWealth
1 week ago | [YT] | 5
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Jerry & Sheila Island Living
🚨 NEW VIDEO — OPERATION LEGACY 🚨
👉 https://youtu.be/5d5yWkmhFbo
If you’re planning to buy or build in the DR, watch this first.
Most people don’t lose money here because of bad luck.
They lose it by stalling, guessing, and paying the Gringo Tax.
This isn’t hype. It’s ground intel:
• how we actually leverage property
• how contractors really price foreigners
• Why execution beats endless research
📍 Santo Domingo
🎯 Assets over aesthetics
🧠 Strategy over vibes
👉 https://youtu.be/5d5yWkmhFbo Watch before you buy.
#OperationLegacy #GroundIntel #GringoTax #DRRealEstate #VeteranWealth #SantoDomingoEste #IslandLiving
1 week ago | [YT] | 34
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