5 Lessons I Learned Building a Real Estate Portfolio in Chicago with family

Over the past four years, I’ve had the opportunity to purchase two multi-unit properties in Chicago. It’s been an incredible journey filled with lessons, challenges, and triumphs. Whether you’re just starting or looking to expand your portfolio, here are five key insights I wish I had known before I began investing.

1. Understand Your Numbers

The first and most critical step in real estate investing is mastering your numbers. When I bought my first property, I underestimated how quickly costs could add up. In Chicago, property taxes can be substantial, maintenance on older buildings can be unpredictable, and heating costs during brutal winters can eat into your profits.

To succeed, run your numbers conservatively. Account for all potential expenses—property taxes, insurance, repairs, utilities, and even property management fees if you’re not handling it yourself. Building a reserve fund for unexpected expenses is also essential. Being financially prepared will give you the confidence to weather any surprises that come your way.

2. Prepare for Chicago-Specific Challenges

Investing in multi-unit properties in Chicago comes with its own unique set of challenges. Many buildings in the city are vintage and may require significant upkeep or even unexpected repairs. You also need to navigate Chicago’s strict landlord-tenant laws and permitting processes. For example, ensuring compliance with local ordinances, like heat and building safety requirements, is non-negotiable.

Proactively addressing these challenges can save you time, money, and stress. Before purchasing a property, have a thorough inspection done and work with professionals who understand the city’s building codes and regulations. The more prepared you are, the smoother your investment journey will be.

3. Build the Right Team

Real estate investing isn’t a solo endeavor. Having a reliable and experienced team around you can make all the difference. Of course, you’ll need a savvy realtor like Edward Grochowiak who understands Chicago’s multi-unit market. He found our first mult-unit purchase off market on Top Agent Network . But beyond that, I recommend finding a trusted HVAC technician, electrician, general contractor, and real estate lawyer.

These professionals will help you navigate everything from unexpected repairs to compliance issues. When a furnace breaks down in the middle of winter or you’re reviewing tenant lease agreements, you’ll be glad you have the right people in your corner. Building relationships with these experts early on can save you headaches down the road.

4. Consider Owner-Occupied Financing

When I bought my properties, I had to put down 25% of the purchase price because they were considered investment properties. While this worked, it tied up a lot of cash upfront—cash that could’ve been used for other investments or emergencies.

If I could do it again, I’d strongly consider moving into one of the units. By making it an owner-occupied property, I could’ve taken advantage of financing options that require as little as 5% down. This approach not only reduces your initial cash outlay but also allows you to build equity while living in your investment.

5. Think Long-Term and Hold Your Properties

For me, multi-unit properties have been more than just investments—they’ve been a way of life. I’ve never lived in a single-family home, and I’ve seen firsthand how rental income can create stability and financial freedom. Growing up, my parents used the rental income from their multi-unit property to cover major expenses like college tuition and family emergencies.

Holding onto properties has been one of the best decisions I’ve made. Real estate is a long-term game, and the benefits compound over time. By keeping your properties, you can build equity, increase cash flow, and create a financial safety net for the future. Multi-unit properties, in particular, offer the flexibility to live in one unit while renting out the others or scaling your portfolio over time.

Final Thoughts

Investing in real estate, especially in a city as dynamic and challenging as Chicago, is a rewarding journey. It’s taught me about financial discipline, resilience, and the importance of long-term thinking.

Whether you’re just starting or looking to grow your portfolio, I hope these lessons resonate with you. Real estate isn’t without its challenges, but with the right preparation, mindset, and team, it can be one of the most impactful decisions you make for your financial future.

If you’re considering investing in Chicago real estate or have questions about getting started, feel free to connect with me. I’d love to share more about what I’ve learned along the way!