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.

I have a coaching exercise called 100 Dreams, which helps clients flex their wish muscles and also reminds them that there isn’t one be-it-and-end-all dream. The popularity of the exercise has resonated with the likes of Chris Guillebeau and Laura Vanderkam, and I’m thrilled they have introduced it into their communities. I do the 100 Dreams exercise for myself, and increasingly my dreams revolve around travel. I could fill the entire exercise with just my dream travel destinations. Of course, there are whole countries on the list, which would need to be broken up into several trips. There are also [...]

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!

One of the things I've had to get used to as a visitor to Costa Rica are all of the dirt roads.  The first time we visited Costa Rica was in the month of March, well after the end of the rainy season and after all of the dirt roads had been fixed and re-graded for the high/dry season and were not hard to drive or navigate. In subsequent visits over the course of the year, I've noticed the roads start to get bumps and ruts, and when the heavy rains come in the summer and fall, the dirt roads [...]