July 21, 2024


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Buying a House in the Caribbean Was Worth It, Despite Challenges


  • I bought a home in Puerto Rico during the pandemic; I plan to retire there, but right now it’s a rental.
  • It hardly earns me anything at the moment, but I don’t care — it made a dream come true for me.
  • I’ve always wanted to retire in the Caribbean, and now I can.

If you ever decide to push yourself to the ultimate limits of your sanity, you should buy a home far, far away during one of the most tumultuous times we’ve ever experienced in modern history. OK, that’s a bit hyperbolic, but it’s quite a feat if you ever want to try it.

I purchased a home on the island of Puerto Rico during the pandemic. Like many people during the last few years, I experienced some extreme emotions and circumstances, which ultimately led me to “jump the shark” and fulfill my retirement dreams about 25 years earlier than anticipated. Here’s how it went down and how it came out for me. 

I took a vacation that led to a house hunt

I am enamored with real estate in every way, shape, and form. So it’s not surprising that while I was vacationing in PR, I found myself up late perusing a home-buying app. What started as “just for funners” scrolling quickly morphed into an I-think-I-may-really-want-this moment. 

A friend of mine, whose parents are from Puerto Rico, decided to fly in and show me around her Puerto Rican neck of the woods. We went to a less touristy side of the island where we found one of the houses I had viewed on the app. 

I loved it: The home was in a residential neighborhood, pretty tiny at 800 square feet, and just a short drive to the beach. I was sold. The realtor, however, wasn’t able to get me into the property before I left, so I made arrangements for a video tour once I came home. 

Then I actually bought the home

The long and short of it is that I eventually put in an offer of about $4,000 over the asking price on the place, intending to keep it as a rental until I can eventually retire there. The neighborhood I chose had properties well under the $150,000 price range, but for me, the purchase was still a big deal! 

Once the offer was accepted, I experienced a range of emotions. On the one hand, I had dreamed of retiring in the Caribbean since my teens when I visited for a study-abroad program. On the other hand, I was not sure it was the greatest idea to get an investment property so far away. The commute from Puerto Rico to Chicago (where I live) is rather expensive — from airport transport to flights and rental cars, it all adds up!

I got it set up as a rental

Although this sounds like a dream job, it was pretty tough. I did have to make a few trips to the island before I could really settle in and start setting the place up as a vacation rental.

Once I was able to make a longer trip there, I ran into another issue. The plentiful, on-demand inventory I was used to stateside was simply not available in Puerto Rico. Some furniture and appliances had wait times of two to six weeks, and Amazon Prime is almost nonexistent there. Plus, the furniture and appliance stores on the island may not have exactly what you want in the time that you want it. 

With this reality, I was forced to pretty much take what was readily available and decorate the house in the simplest, most cost-effective way possible. In the interim, I had to deal with contractors, service providers, customer service representatives — and many times in Spanish. 

Although my Spanish is pretty good, I need to point out that Puerto Rican Spanish is one of the most difficult dialects to learn and understand (to me). This partial language barrier just added another barrier of frustration to my activities there. 

However, after all the heartache and pain, the place runs pretty smoothly as a short-term rental. All my expenses add up to around $900 per month (not including debt service to a private lender set to end next year) with anywhere from $1,000 to $1,200 a month in bookings. The profit is pretty tiny now, but in a few years, I expect my rates to increase and provide the cash flow I need until I am ready to live there. 

What I learned from the experience

Going to Puerto Rico and buying a home might sound like a dream, but I can tell you that it was one of the most difficult things I’ve ever done in my life. There were so many factors at play — from making a long-awaited dream come true to the frustrations of doing business in another culture and language and facing ever-changing pandemic dynamics. 

I came to the island with my expectations and had to totally reorient myself to a different reality. Sometimes it was refreshing, while at others, it was pure exasperation. Even in all of this, I accomplished a goal much earlier than I had initially planned. 

As a plus, I’m able to provide a comfortable, affordable vacation option for families that want to experience the wonder and beauty of Puerto Rico. Not only have I hosted a number of vacationers at my place, but I’ve also welcomed family and friends who’d never experienced things like snorkeling, hiking a waterfall, or world-famous Puerto Rican frappes.  

The lessons I learned in this endeavor were many, but the takeaway is that your dreams could be much closer than you think. On the flip side, they could also require more work than you ever thought. In the end, the stretching and the challenges can be worth becoming a new, better person in the process. So for me, this was a win. I am glad I did it and would do it over again if I had the chance!


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