Before our first trip to Costa Rica in March 2017, we had checked out the Philippines two months earlier. Scott, our oldest daughter and I took a 2-week trip to Manila in January 2017 – their first trip and my fourth, although my previous trip was 25 years ago, so it felt like my first time too. I was already primed to possibly live there because the favorable exchange rate (currently over 50 Philippine pesos to one US dollar) meant that we could drop everything and retire -- no job required -- right now.

In our first trip to Costa Rica, we split our week between Tamarindo (the “Gold Coast”) and Ojochal (the “Southern Zone”). These were two areas we had read about, and we wanted to compare them back-to-back. We opted to start our Costa Rica journey with a small condo in the heart of the Gold Coast, walkable to everything. It suits our needs for a hassle-free, income-producing, and driverless vacation property. Now that we have two Gold Coast properties in our portfolio, maybe we’ll reconsider the Southern Zone. I’m afraid to look at where prices have gone even in just one year.

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.

When we decided to buy real estate abroad, one of the critical steps was figuring out where we would get the money to buy. Since we had settled on desirable Tamarindo, we knew that properties would sell relatively quickly so we would have to decide quickly and be able to close quickly (or at least show we could close quickly). Here are eight options we considered for financing our international purchases.

I'm not exactly a football / soccer fan, but any interest I have in the sport is directed to my home team, the New York Red Bulls.  Yes, technically the NYFC team in New York City (known as The New York City Football Club) would technically be my home team as the Red Bulls play in New Jersey and NYFC plays in Yankee Stadium in my home borough of the Bronx, but I dislike to a fault all things Yankees, so the Red Bulls are my team.  Over the years, I've been to two games in Red Bull Arena in [...]

With 15 properties in our portfolio and a tendency to be risk-averse, I think a lot about how quickly and in what order we should pay off mortgage debt. We own six of our rentals free and clear – i.e., zero debt – but that leaves nine mortgages, including our primary residence. Our loans have different balances, different interest rates and different maturities. I rank ordered our mortgage debt based on four pay-off strategies and then took an average ranking to see which ones we should focus on paying off first. See below for the analysis we used to rank [...]

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 get the deal done, we did have to relax some of our investment rules that act as checks and balances. Here are the three investment rules we broke and why we felt it still made sense to go ahead with the purchase: One of the [...]

Our oldest daughter is finishing up her last year of college. She got a full tuition scholarship to a city college, which saved us over $200,000 over four years vs going to a private college, an opportunity cost large enough to buy a house outright for cash! While we didn't do that, we invested that money in her future in other ways, including real estate. While we dodged the college-tuition bullet there, the college monster rears its ugly head again, as our youngest daughter is now less than two years away from entering college. She’s looking at both city college [...]

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.