Jerry & Sheila Island Living

Most people moving to the DR fail because of one specific mistake. Can you guess which one it is?

2 days ago | [YT] | 23

Jerry & Sheila Island Living

I got tired of the "US Tax" on my life. 📉

We weren’t just "moving to the Caribbean," we were escaping a system of $450 overdraft notices and 30% real-world inflation. One year later, we’ve turned that around into a +22% gain.

This photo of us in the DR represents the "after," but the "before" was stressful. In my latest video, I’m pulling back the curtain on our actual 2026 budget here:

The "AC Trap": Why your housing costs might skyrocket if you aren't careful.

The 30% Reality: Why the official inflation numbers are lying to you.

Healthcare & Debt: How we cut the cord on US economic stress.

If you're feeling stuck or just want to see how the math actually works for an expat life, watch this.

Watch the full breakdown here: https://youtu.be/NbEV2Ro4PQE

2 days ago | [YT] | 71

Jerry & Sheila Island Living

The video I dropped yesterday? That was just the introduction.
I’m already back in the lab working on the next piece of the puzzle. Most people celebrate the upload; I celebrate the execution of the next step.
If you thought the last video was valuable, you have no idea what’s coming next. Keep up.

2 days ago (edited) | [YT] | 73

Jerry & Sheila Island Living

One of our subscribers is single and planning to live in Santo Domingo on $2,500 USD/month. Based on current inflation and lifestyle, is this realistic?

3 days ago | [YT] | 17

Jerry & Sheila Island Living

The US economy is in an overdraft state, but your life doesn't have to be. 🛑 While the stateside cost of living is drowning veterans and families on fixed incomes, we’ve found a way to secure a +22% monthly gain here in the DR. even with a car note and child support.

We aren't just showing you the beach; we're showing you the spreadsheet. 📊 The 2026 numbers are out, and it’s time to stop surviving and start strategically winning.

Watch the full breakdown here: https://youtu.be/NbEV2Ro4PQE

3 days ago | [YT] | 36

Jerry & Sheila Island Living

Family isn’t perfect, but it’s real. It’s built on sincere hugs, unexpected kisses, and looks that say everything without needing words.

Here we are, continuing the journey—learning along the way, growing together, and valuing every moment we share. Grateful to God for the blessings, the lessons, and the opportunity to keep moving forward together 🙏✨

Thank you to everyone who supports us and is part of this community 🤍

#RealFamily #Love #Grateful #Faith #RealLife #FamilyFirst

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5 days ago | [YT] | 213

Jerry & Sheila Island Living

✨ Gratitude, consistency, and excellence ✨

Today we celebrate with a full heart ❤️
10 consecutive quarters as a Superhost 🏆
215 stays
⭐ 5-star rating
❌ 0% cancellation rate
💬 100% response rate

Thank you to every guest who trusted us, appreciated the details, and left such kind words. This achievement is the result of hard work, dedication, and genuine care to make every stay a memorable experience.

We will continue giving our best, taking care of every space, and welcoming our guests with open arms 🤍🏡

On to many more! ✨🙏

#Superhost
#Grateful
#ProudMoment
#HospitalityWithHeart

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1 week ago | [YT] | 22

Jerry & Sheila Island Living

Most people see the destination; they don't see the shifts, the risks, and the long hours behind the scenes. Every video I edit and every move we make is for him. This isn't just about a change of scenery, it's about changing our family’s trajectory.

What’s the 'Why' that keeps you going when the work gets heavy?

1 week ago | [YT] | 152

Jerry & Sheila Island Living

You’ve seen how $3,700/mo in VA Disability changes the game in the DR. But I know many of you are planning your "Bridge to Freedom" using multiple income streams. I want to make sure my next deep dive gives you the exact math you need for your situation.

Which financial pillar do you want me to dissect next? 🇩🇴💸

1 week ago | [YT] | 12

Jerry & Sheila Island Living

She speaks Spanish, I speak English. People ask how we manage the day-to-day. The truth? We don’t waste time on noise—we focus on alignment.

Whether it’s navigating a trail or building a life, if you’re headed in the same direction, the "how" takes care of itself.

I’ve broken down the full strategy on how we maintain this level of clarity (and how you can apply it to your own goals) over on the site.

Different languages, same direction. 🏁 Diferentes idiomas, misma dirección.

Read the full breakdown here: www.jerrysheilaislandliving.com/post/dating-in-the…

1 week ago | [YT] | 87