Jerry & Sheila Island Living

Be honest. In 2026, can a single veteran actually thrive (not just survive) on 100% VA Disability ($3,700) in the United States?

2 hours ago | [YT] | 3

Jerry & Sheila Island Living

https://youtu.be/aT4FrOUFMP4?si=Ay7ba...

2 hours ago | [YT] | 8

Jerry & Sheila Island Living

Following up on our last photo: When is your "Island Reset" happening?

5 days ago | [YT] | 12

Jerry & Sheila Island Living

We’re already in 'Island Reset Mode' for 2026. 🇩🇴 Who else is making the move this coming year? We want to know where you guys are in your journey.

We are posting a poll right after this—keep an eye out and cast your vote! 👇

5 days ago | [YT] | 71

Jerry & Sheila Island Living

www.jerrysheilaislandliving.com/book-online
We live the life you're trying to figure out.

Sheila and I didn't get here by accident. We got here by having a plan.

I get DMs every day asking "how to start" or "is it safe?" The reality is, I can't answer your specific financial and life situation in a YouTube comment.

If you are actually serious about expat life, real estate, or business in the DR, you need a strategy, not just a dream.

Book a consultation. Let’s look at your numbers and make it real.

👇 BOOK HERE: www.jerrysheilaislandliving.com/book-online

6 days ago | [YT] | 19

Jerry & Sheila Island Living

From Cali to Santo Domingo! ✈️
We love it when the online community becomes real life. Shoutout to this couple from California who swung by the house while in town visiting family. It was great sharing stories about life in the DR vs. the States. The circle is growing.
Where are you watching from today? Drop your flag in the comments

1 week ago | [YT] | 168

Jerry & Sheila Island Living

🛑 Stop guessing which neighborhood is safe.
👇 Read the full guide here:
www.jerrysheilaislandliving.com/post/safe-sound-th…
We get asked every single day: "Is Santo Domingo actually safe?" The honest answer? It depends on the street.

We just updated our blog with a brand new Comparison Table breaking down the Top 5 Neighborhoods for Expats. We compare them by: ✅ Safety Rating (Veteran Approved) ✅ Walkability & Vibe ✅ The "Red Zone" areas you need to AVOID.

Don't guess with your safety. Get the facts from a US Veteran and a Local.

1 week ago | [YT] | 40

Jerry & Sheila Island Living

DID YOU MISS THE PARTY? 🥳🇩🇴

The replay is officially UP! We had such a blast celebrating Jendry’s 1st Birthday yesterday. If you want to see a true Dominican birthday fiesta, you have to check this out.

What you missed: 🎂 The Cake Smash (it got messy!) 🪅 Jendry vs. The Piñata ❤️ A special moment singing "Cumpleaños Feliz"

Thank you to everyone who joined us live! If you missed it, catch the replay here: 👇👇👇 youtube.com/live/LthXM61uRn8?feature=share

1 week ago | [YT] | 175

Jerry & Sheila Island Living

🎉🎂 Today our little king turns ONE! 🎂🎉

It’s Jendry’s 1st birthday 🥹🙏🏽
One full year of love, growth, sleepless nights, laughs, and blessings we never saw coming.

If you’ve been rocking with our journey, take a second and drop a HAPPY BIRTHDAY for Jendry in the comments 💙🇩🇴
We want him to look back one day and see how much love he had from the Island Living fam.

Thank you all for being part of our story and watching our family grow.
We don’t take this support lightly — it means everything.

🎈🎉🎂
Thanks for watching fam! 🙏🏽👊🏽
#jerrysheilaislandliving #jerryandsheilaislandliving

1 week ago | [YT] | 162

Jerry & Sheila Island Living

On a day like today, my son Jendry was born ✨
That day, time changed its rhythm, the heart understood its true purpose, and life took on a meaning greater than any plan. You arrived to remind us that miracles exist, that love multiplies, and that some blessings can’t be explained—they’re honored every single day.
Happy life, my greatest gift 💙🙏🏽👊🏽
#jerrysheilaislandliving #jerryandsheilaislandliving

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1 week ago | [YT] | 77