To Sell or Not to Sell: Is It Time to Trade Up Your Rental Properties?

For many investors, the question arises sooner or later: Should I sell my smaller rental properties to scale up into something larger?

At Stephan Group Brokerage, we hear this question all the time. Often, it comes from investors who own one or a few small, cash-flowing rental properties but are eyeing the power and potential of scaling up.

This exact dilemma led me to make one of the biggest decisions of my real estate career.

My Journey: Selling Small Rental Properties to Scale Big

Back in 2023, I faced a pivotal moment. I decided to sell four of my cash-flowing duplexes and my fourplex to execute a massive—and let’s be honest, stressful—1031 exchange into a 56-unit apartment complex.

The stakes were high, but so were the potential rewards. Along the way, I learned invaluable lessons that I now share with fellow real estate investors who are considering similar moves.

Key Lessons I Learned While Scaling Up My Real Estate Portfolio

In my latest YouTube video, I break it all down step by step. Here’s a preview of what I cover:

• Was Selling My Smaller Rental Properties to Buy Big the Right Move? Scaling up sounds exciting, but I reflect on whether selling smaller, stable rental properties for a larger, more complex one was the best decision.
• How I Avoided Taxes Through a 1031 Exchange Taxes can eat into your profits, but with proper planning, they don’t have to. I explain how the 1031 exchange helped me defer taxes and maximize my real estate investment.
• A $500M Investor’s Litmus Test for Selling A seasoned investor shared a simple but powerful litmus test with me to determine when it’s time to sell. I reveal this strategy and how it guided my decision-making.

Watch the full video here: Why I Sold All My Duplexes to Buy a 56-Unit Apartment. 

Thinking About Trading Up Your Rental Properties?

Scaling your real estate portfolio isn’t a one-size-fits-all decision. It requires a clear understanding of your goals, resources, and risk tolerance. In the video, I share real-world insights and give you the tools to make an informed choice for yourself.

If you’re considering selling smaller rental properties and trading up—or just want to see how I navigated this process—check out the video here.

After watching, I’d love to hear your thoughts. Leave a meaningful comment on the video and share your own experiences so we can continue the conversation about what it takes to grow in real estate investing.

The bottom line is that scaling up may feel daunting, but with the right strategies and insights, it could be the key to unlocking your portfolio’s full potential. Subscribe to my YouTube channel for more insights into the real life of a successful Michigan real estate investor. Or, if you’re already investing in Michigan real estate or want to start, reach out to us at Stephan Group Real Estate. Our team will be happy to help you achieve your real estate goals. 

We’re in this together!