If you had told us back in 2005 that real estate would become a core part of our lives — not just financially, but in how we grow, make decisions, and even raise our kids — we probably wouldn’t have believed you. But here we are, nearly two decades later, with properties in four states, investments across several more, and a whole lot of hard-won lessons in our back pocket.

This blog is our attempt to reflect, share, and maybe offer a little guidance to anyone thinking of walking a similar path.

Our Early Days: Lessons the Hard Way

We started like a lot of people — buying our primary residence in 2005 (a condo), followed by a rental condo out-of-state in 2007. The timing? Not great. The strategy? Honestly, not much of one. We didn’t focus on the right properties in the right neighborhoods, run the numbers with the right lens, we underestimated costs, and yes — there was a touch of FOMO in our decisions.

By 2014 and 2015, we sold both properties at a significant loss. It hurt. But it also forced us to reevaluate and re-educate. And those early failures turned out to be some of the best (and most expensive) teachers we’ve ever had, helping us to make much more thoughtful, informed decisions going forward.

Pivoting With Purpose

We didn’t give up. We dove deeper into learning what actually works in rental real estate — not just the success stories, but the real nuts and bolts: rents vs. costs, team-building, neighborhood dynamics, financing structures, risk management.

In 2011, we started again — buying three single-family homes in Arizona. This time, the fundamentals lined up: prices were far below replacement cost at the time, rent covered all the real expenses (not just the basics), and we secured long-term fixed-rate financing.

Around the same time, we also bought a 2-plex in a tough California neighborhood. On paper, it looked good. In reality, managing from afar in a tough neighborhood (even with a property manager) proved much harder than we expected. It taught us that real estate isn’t just about the numbers — it’s about competence, control, and knowing your limits.

The Value of Local and Hands-On Management

In 2013, we bought a 4-plex near where we live. We saw room to improve it and bring in great residents. It worked — but not without challenge. One eviction of a resident that we inherited from the prior owner stretched for months and ended with the unit badly damaged. It was a tough reminder: even when you do everything you can and do it with best practices, things can go wrong. But the key is staying focused on your long-term goals and not letting setbacks derail your plan.

Growing and Reinvesting Through 1031 Exchanges

As Arizona appreciated, we used 1031 exchanges to sell those early properties and buy into San Antonio. Each Arizona property helped us buy multiple rentals in Texas. We used fixed-rate loans and even refinanced to pull out our original cash while still owning the assets.

Sounds ideal, right? Mostly — but Texas had its own curveballs. Unlike Arizona, property taxes and insurance in Texas escalated quickly. Some of our tax bills and premiums doubled or tripled. It reinforced a hard truth: your numbers might pencil out at purchase, but you must leave room for the unexpected.

Scaling Up and Self-Managing

In 2019, we returned to Arizona to buy two small apartment complexes, again through 1031 exchanges by selling some of the San Antonio properties. This time, we took a more hands-on approach and eventually shifted to fully self-managing — not just locally, but across all our out-of-state properties. It takes work to develop your team, really understand your properties and effectively resolve the day to day issues that come up, but it gives us more control and a better connection to our residents and properties.

By 2021, we sold one of those apartment buildings (again in a 1031 exchange) and used the proceeds to buy several smaller multi-family properties in Kansas City — plus investments in Delaware Statutory Trusts (DSTs) to create more passive income and diversify further. The DSTs gave us exposure to new markets without the direct management responsibilities — though they come with lower returns and higher fees.

Lessons From Syndications and Passive Investing

We’ve also invested as passive limited partners in private real estate deals (syndications) for over 15 years. Some were great. Some… not so much.

Here’s what we learned:

• A syndicator’s track record doesn’t always mean they truly understand risk — especially when the last decade made a lot of people look smart.
• Relationships among general partners matter. We’ve seen disputes derail otherwise great investments.
• Stick to your core beliefs. We broke our own rule in 2021 by investing in a deal with variable-rate debt — and paid the price when interest rates spiked in 2022.

A Family Mission

One thing we’re proud of? We’ve done this journey together — as husband and wife, as partners, as a team. My wife brings the human touch, the relationships, the team-building, the resident interactions. I focus on the numbers, the documents, the systems. We complement each other, as I think we do in a lot of areas of our partnership.

And now, we’re bringing our kids into the picture. Not just so they inherit property, but so they understand what it means to be responsible, engaged owners. We want them to learn that rental real estate isn’t a get-rich-quick scheme — it’s a long game. One that can give them flexibility, freedom, and a strong financial foundation for them to pursue their life’s dreams and goals.

Final Thoughts

We’ve made mistakes. We’ve taken our share of lumps. But every bump has helped shape who we are — smarter, more resilient, more thoughtful investors.

If you're thinking of stepping into real estate, here’s what we’ll leave you with:

• Keep learning. There’s always someone with more experience you can learn from.
• Stick to your principles. Especially when the market tempts you to chase returns.
• Build a strong team. And treat everyone with professionalism and respect.
• Control what you can. But understand that uncertainty is part of the deal.
• Work together. If you’re in this with a partner, make sure your values and vision are aligned.

This is our journey — and it’s still ongoing. We’re excited to see what comes next. We’d love to hear from you, if you’d like to hear more about any part of this journey, or any other real estate questions that you might have, especially as they relate to your own journey!