Retirement planning perspectives

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.

For centuries, rental real estate has stood the test of time as a reliable vehicle for building wealth, generating income, and preserving capital. Even in today’s fast-paced, tech-driven investment landscape, it remains one of the most favored strategies for long-term financial independence—and for good reason.

Here’s a look at why rental real estate continues to be a powerful, multi-dimensional investment, backed by data and time-tested fundamentals.

Real estate is often seen as a solo pursuit—one investor, one property, one big decision at a time. But in reality, real estate is the ultimate team sport. Whether you're acquiring your first rental property or managing a portfolio across multiple states, your success hinges not just on what you know, but who you know and how well you work together.

Over time, we've learned that one of the most valuable skill sets an investor can develop is the ability to build and foster long-term relationships with a team of experienced, knowledgeable, accountable, and honest professionals. Let’s walk through the key phases of real estate investing—Acquisition, Ownership & Management, and Sale—and explore the essential team members who play a role at each stage.

Over the past two decades, my family and I have built a residential rental portfolio that supports our long-term goal of financial independence. Along the way, we’ve learned a ton—from other investors, mentors, books, trial-and-error, and plenty of hands-on experience. We followed a set of guiding principles and investment criteria that have stood the test of time—and changing markets.

Before diving into the nuts and bolts, let’s start with some perspective. According to data from the U.S. Census Bureau and the Rental Housing Finance Survey, there are over 20 million rental properties in the United States. 70% of these are owned by individual investors, not institutions or corporations. Of those, roughly 17 million consist of small, 1-4 unit properties. That’s the segment we’ve focused on for much of our investing journey, although we have owned (and continue to own) small apartments along the way.

It’s a common and exciting life milestone: you’re moving! Maybe you’re upgrading to a bigger home, downsizing for retirement, relocating for a job, or wanting to be closer to family. Whatever the reason, you’re now facing an important financial decision — what should you do with your current home?

If you have enough liquidity to buy your next property without selling your existing one, you might be tempted to keep your old house and rent it out. It feels logical: why sell a familiar property that could generate passive income?

In fact, according to the National Association of Realtors (NAR), approximately 10-15% of homeowners choose to convert their primary residence into a rental property when they move, rather than sell it outright. It's a relatively common path — but does it actually make financial sense?

The answer: Probably not.

Here’s a deep dive into why — and when it might still make sense.