Jerry & Sheila Island Living

Operation Legacy: How We Built Our DR Airbnb (And Avoided the Gringo Tax)
https://youtu.be/5d5yWkmhFbo

19 hours ago | [YT] | 25

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

20 hours ago | [YT] | 3

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

21 hours ago | [YT] | 23

Jerry & Sheila Island Living

From Airborne paratrooper ➝ island life 🇩🇴

We didn’t retire to sit still. We built.
Two Airbnbs. A family. A new mission.

Same discipline. New battlefield.

If you’re thinking about starting over, understand this:
freedom is earned again, just in a different uniform.

Appreciate everyone rocking with us on this journey. More game coming soon.

2 days ago | [YT] | 167

Jerry & Sheila Island Living

Building wealth doesn’t always look like hustle culture.
Sometimes it looks like patience, smart Airbnb plays, and putting assets to work in the Dominican Republic 🇩🇴🏝️

We didn’t chase hype; we focused on cash-flow, location, and systems.
One unit at a time. One lesson at a time.

If you’re thinking about Airbnb, real estate, or geo-arbitrage in the DR, this journey is for you.
More game coming soon.

4 days ago | [YT] | 87

Jerry & Sheila Island Living

What’s stopping you from investing in real estate in the Dominican Republic?

6 days ago | [YT] | 9

Jerry & Sheila Island Living

This didn’t happen overnight. It happened because y’all kept showing up, watching, commenting, agreeing, disagreeing, learning, and rocking with us through the real stories of life in the DR.

From expat life to relationships, money, mistakes, and wins... We document it all, unfiltered.

Next stop: 10,000. If our content has helped you in any way, make sure you’re subscribed and share the channel with someone who needs the truth before making the move.

Much love to the Island Crew. More work to do. 🙏🏽👊🏽
#jerrysheilaislandliving #jerryandsheilaislandliving

1 week ago | [YT] | 141

Jerry & Sheila Island Living

Compensation is NOT a Handout.
https://youtu.be/tP-b6QRFb7Q

There is a massive misconception that VA disability is a form of welfare. Let’s set the record straight: Welfare is based on need. VA Disability is based on service-connected impact. You didn’t "win the lottery," and you aren't "beating the system." You paid for this with your health and your time. Whether you live in the States or abroad, and whether you’re struggling or thriving, that compensation is yours by right.

Stop letting people make you feel guilty for a benefit you earned in uniform.

1 week ago | [YT] | 36

Jerry & Sheila Island Living

If you faced a major setback after a long career, what would be your "Plan B"?

1 week ago | [YT] | 7

Jerry & Sheila Island Living

https://youtu.be/tP-b6QRFb7Q
They reported me… but the truth didn’t change.
This one almost didn’t get posted. Watch before you judge 👀👇
Thanks for watching fam! 🙏🏽👊🏽 #jerrysheilaislandliving #jerryandsheilaislandliving

1 week ago (edited) | [YT] | 67