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
I’m planning our upcoming deep dives into DR real estate and island life. To make sure you don't miss the critical details, when do you usually have 10 uninterrupted minutes to watch a full video?
🌍 Other (Drop your time zone/time below)
15 hours ago | [YT] | 12
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Jerry & Sheila Island Living
We are less than 600 subscribers away from our 10,000 goal!
This journey started with a simple move to the island, and now we’ve built a community of thousands exploring the DR together. If you’ve found value in our videos or just love island life, hit that subscribe button and help us cross the finish line today.
Who’s going to be number 10,000?
1 day ago | [YT] | 55
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Jerry & Sheila Island Living
When it comes to "jealousy" in a relationship, where do you stand?
1 day ago | [YT] | 4
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Jerry & Sheila Island Living
https://youtu.be/1hk1h8JIzAk
Is it "jealousy" or just deep investment?
We’re breaking down one of the biggest cultural stereotypes in the Dominican Republic. Sheila and I dive into why "doing you" might actually be a red flag and what real commitment looks like in a Dominican household.
We’re done with the fluff; this is the unfiltered truth about relationships, boundaries, and building a life with strategic depth.
Take the Quiz in the video to see if you really understand the culture!
👇 WATCH THE FULL VIDEO HERE:
https://youtu.be/1hk1h8JIzAk
1 day ago | [YT] | 24
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Jerry & Sheila Island Living
I hear you loud and clear! 👂
First off, thank you to everyone who voted in my poll yesterday. The results were eye-opening: nearly 80% of you feel that content should be free or that 1-on-1 advice only takes "a quick minute."
I get it. When Sheila and I started this channel, it was all about sharing our journey and helping the community. That hasn't changed. We love providing free value here every single week! 🌴
However, here is the "Real Talk" from my side of the screen:
While a "quick question" seems small, answering dozens of them every day adds up to hours of work behind the scenes. To keep the lights on and the high-quality videos coming, I have to be smart about where I spend that energy.
Moving forward, here’s how we’re going to balance things:
Free Community Value: I will keep posting videos and tips, and I will continue to answer general questions in the comments for everyone to see.
The "Quick Question" Solution: If you have a specific question, ask it in the comments! If it’s a great topic, I’ll make a video about it so the whole community benefits.
1-on-1 Deep Dives: If you need a private, tailored strategy for your specific move or investment that I need to pay attention to, that is where our formal consultations come in.
We want to keep growing this community without the pressure, while also making sure we're around for the long haul.
Thanks for being part of the journey and for the honesty in the poll!
4 days ago | [YT] | 124
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Jerry & Sheila Island Living
Why do people expect 1-on-1 advice from content creators… but don’t want to pay for their time?
6 days ago | [YT] | 12
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Jerry & Sheila Island Living
When you think of "Island Living," what’s the actual goal?
1 week ago | [YT] | 21
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Jerry & Sheila Island Living
If you were getting out today, what’s your REAL plan?
2 weeks ago | [YT] | 7
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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?
2 weeks ago | [YT] | 43
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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 🙏🏽👊🏽
2 weeks ago | [YT] | 64
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