On our first trip to Costa Rica, while driving around the different beaches in the Guanacaste area, we stumbled on an Open House sign for a development near Playa Flamingo. We saw multiple lots, where we could develop a property, and we also saw an already built spec home we could have immediately.

It was 1,950 square feet, with 3 bedrooms and 2 baths. It had a garage and infinity pool, with a view of the ocean in the distance. It was listed at $399,000.

We ended up passing on the home, and here’s what factored into that decision.

We bought our first multi-family property – a duplex in the trendy Riverside area of Jacksonville, Florida – and broke three investment rules in the process. We did our due diligence (e,g, property inspection, cash flow calculations) and felt that the opportunity matched our philosophy of cash flow and value over the long-term. But to […]

We first visited Costa Rica in March 2017 and closed on two properties before the end of the year. For our first property, we knew we wanted to be in Tamarindo, a popular beach town. Our intent was to buy a vacation rental investment for now, and “popular” ensures strong rental potential and “beach town” fits in with our priority to retire by the water.

Buying in Costa Rica was important to us because we look at it as our FIRE Plan B – if we can’t afford to retire early in pricey New York City, we could definitely do it here.

After our second child arrived in 2001, our New York City apartment felt smaller and smaller.

We always had a strong interest in buying real estate, but never pulled the trigger. A big regret was not buying a top floor duplex apartment in a small building in the Kips Bay section of Manhattan in the mid 90’s. In our defense, we were less than 2 years out of college and it would have been a financial stretch to do so.

But before long, that several-hundred-thousand-dollar apartment would be worth more than a million. What an investment that would have been!