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  • Home
  • Countries

    Top Destinations:

    Whether you’re looking for fun and sun, a peaceful retirement, or the chance to earn some extra income, you’ve got a real world of opportunity open to you… In short, we’ve done our best to narrow down your best options, but only you can decide the right country for you.

    • Spain
    • Portugal
    • Panama
    • Belize
    • Colombia
    • Cyprus
    • Mexico
    • France
    • Montenegro
    • Browse All Countries

    Best For:

    • The Best Places To Retire
    • Health Care Abroad
    • Cost Of Living
    • Investing in Real Estate
    • Establishing Residency
    • Gun Laws In The World
    • English-Speaking Countries
    • Safest Places For Retirement
    • Best Places In Latin America
  • Budgets

    How Much Will It Cost You To Live Overseas?

    The only honest answer is, we have no idea. And neither does anyone else. The only one who can answer that question is you. Here’s the most important thing to understand about budgeting your new life overseas…

    Super Cheap

    • Chitré, Panama
    • Santa Marta, Colombia
    • Phuket, Thailand
    • Dumaguete, The Philippines

    Cheap

    • Medellin, Colombia
    • Boquete, Panama
    • Kyrenia, Cyprus
    • Hua Hin, Thailand
    • The Algarve, Portugal

    Affordable

    • Valencia, Spain
    • Cascais, Portugal
    • Las Terrenas, The DR
    • Pisa, Italy
    • La Rochelle, France
    • Mazatlán, Mexico

    Luxury

    • Ambergris Caye, Belize
    • Kotor, Montenegro
    • The Panama City Beaches
    • Paris, France
  • Resources

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    Follow Us:

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  • Real Estate

    Buying Real Estate For Cashflow

    • Discover tips and strategies used by global property investing veterans

    Explore Our Latest Posts

    • Learn how to invest and purchase property abroad…

    Go To The Overseas Property Alert Site

    • How To Become Independently Wealthy And Fund The Lifestyle Of Your Dreams
  • Conferences

    Upcoming Events

    • Explore Our Events Site

    Live and Invest In Spain Conference

    Offshore Wealth Summit

    Greece Workshop

    VALENCIA, SPAIN

    Sep. 17-19, 2025

    PANAMA CITY, PANAMA

    Oct. 15-17, 2025

    VIRTUAL

    Nov. 13, 2025

    LEARN MORE
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    LEARN MORE
    PRE-REGISTER
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    overseas living letter offers affordable retirement guidance
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Home Investing

A Surprise Legacy Investment

by Lief Simon
Jun 10, 2024
in Investing
0 0
View from a wooden cabin in a mountain

AdobeStock/Chris Gardiner

Sometimes real estate is a longer-term hold than you expect.

I usually go into any property purchase with a plan to hold for at least three to five years. I’ve held properties much longer, but rarely have had a round trip in less than three years.

Buy to renovate and flip and your timeline might be as little as 12 months, depending on how much work you’re doing on the property. I know a guy who was able for a short time to buy properties, do minor repairs, paint, and flip. He was in and out in less than six months.

Of course, the upfront research time for the individual properties took time and a fair amount of effort.

Pre-construction condos can turn around in less than three years depending on the construction time and whether or not you can sell the unit before the building is completed. I did this only once in my years of real estate investing overseas. It was a beachfront condo in Estepona, Spain, when the market was starting to get frothy.

Land speculation is a different animal.

I’ve owned this parcel of land in Canada for about 20 years. It’s on an island in Nova Scotia…

A developer friend originally bought the land (on an island known as McLean Island), carved it up into lots, and ran basic infrastructure.

The idea was to flip the lots within three years.

The reality is that only a few of us who bought in sold that quickly. The market had softened by the time the development process was completed.

In the years since, I’ve listed the property every once in a while, with no bites.

Meanwhile, I wasn’t put out holding onto the property. It didn’t cost much and the property taxes weren’t anything to speak of… and it’s 7 acres of wooded oceanfront.

Then the pandemic ended and the real estate agent I had last listed with wrote to ask if I was still interested in selling. A quick family meeting and the answer was no.

My son, Jackson, didn’t know we owned the land. When he found out, he asked if we could build a log cabin for family trips that we could rent out when we weren’t using it.

That suggestion worked for me as long as he took the lead, which he told me he was up for doing. I don’t have time to build a log cabin in Canada right now.

Twenty years after buying the land, we visited it for the first time last month…

Kathleen and Lief in Canada… And A Family Project

The idea of building a log cabin on an island is romantic, but we figured we’d better go see the island for ourselves before committing to the plan.

So, we made it our annual family holiday.

This is a wild and beautiful part of the world—a true escape. It’s super-safe and life is simple. There’s lots of wide-open spaces and dramatic coastline…

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It was a lot of fun scouting out the 7 acres, thinking about the best place to build a cabin.

Here we are meeting a man about our plans…

A log cabin in CanadaOur land has 70 years of growth on it—and no one has done anything on the land for at least 20 years. There were lots of fallen trees from hurricane Fiona last September…

We bought chainsaws and hatchets and me, Jackson, and my son-in-law Harry spent a day lumberjacking.

We cut a path through the forest to reach the coast… (see, no fires were needed for us to clear our property.)

The island was right next to some of the wildfires—and was covered in smoke. But it wasn’t so bad deep in the woods where we were cutting…

Next Steps

We started to develop a connection to the land while we were there…

I’m very glad we made the trip. But I still haven’t worked out the exact next steps in our cabin-building plan…

We started speaking with a company that does pre-fabricated log cabins, but everyone else was busy for the summer season already—they didn’t have much time to even talk with us.

Then the fires started which took everyone’s attention…

Each person we spoke with for advice or help, only knew their part of the process. When I tried to get the name of someone who could help manage the entire project… no one knew what to say. The locals didn’t know anyone who did that. It seems that the landowner usually functions as the planner and the general contractor for their own project…

We need a surveyor to lay out the plan for where to build on the property… and where to put the septic. One surveyor told us we probably could only build one structure. Another told us it was just one septic system that was allowed per lot… no matter the size of the lot. Assuming the second guy was correct, that means we need to plan the entire compound first and then install a septic system big enough for all future construction. No one really knew how to think about that.

We have some contacts and will start conversations via email… but Jackson will have to go back in person to really make progress.

The scouting trip fulfilled its purpose… Jackson is still eager to work on the project after the visit.

My 20-year-old, 7-acre land investment in the Canadian wilderness has evolved from a potential quick flip to a family legacy undertaking… and a father-son project.

I can’t imagine a better investment than that.

Stay diversified,

Lief Simon signature

Lief Simon

Editorial Director, Global Property Advisor

Tags: 'investing''investment''overseas investing''real estate'CanadaInternational Property SummitLegacy Investment
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Lief Simon

Lief Simon

Lief Simon has lived and worked in 7 countries on 5 continents and traveled to more than 75 countries. His real estate investment career began with a $5,000 down payment on a three-flat building in Chicago. Less than three years later, Lief sold the building for a leveraged return of 3,000%—$150,000 in profit after closing costs and commissions.

From there, he turned his attention overseas and has bought property in 24 countries including France, Croatia, Portugal, Ireland, Belize, Spain, Argentina, Cyprus, Romania, and beyond. Thanks to his decades-long career as a global property investor, Lief has built a multi-million-dollar portfolio that includes rental properties, significant land holdings, and 7 personal residences.

Lief has established residency in 3 countries and acquired a second passport from Ireland.

In 2008 Lief and wife Kathleen Peddicord made the most important investment of their lives—a 215-acre oceanside finca, known as Los Islotes. There, on Panama’s largely undiscovered Veraguas coast, they’ve installed underground electricity, water, and internet and built a forever family home that sits at the heart of their ultimate vision: a gold standard private residential community for those in search of a true safe haven escape.

Lief’s latest book, “Cowboy Millionaire—The New American Pioneer,” collects all the wisdom he has learned in three decades of living and investing outside America.

He offers advice on international diversification in his twice-weekly Offshore Living Letter and monthly Simon Letter dispatches. For real estate investment opportunities, check out his monthly Global Property Advisor service.

If you’d like to meet Lief in person, join him for one of our upcoming in-country conferences. You’ll find further details here.

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To Live Overseas?

Super Cheap

  • Chitré, Panama
  • Santa Marta, Colombia
  • Phuket, Thailand
  • Dumaguete, The Philippines

Cheap

  • Medellin, Colombia
  • Boquete, Panama
  • Kyrenia, Cyprus
  • Hua Hin, Thailand
  • The Algarve, Portugal

Affordable

  • Valencia, Spain
  • Cascais, Portugal
  • Las Terrenas, The DR
  • Pisa, Italy
  • La Rochelle, France
  • Mazatlán, Mexico

Luxury

  • Ambergris Caye, Belize
  • Kotor, Montenegro
  • The Panama City Beaches
  • Paris, France

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