I took a gamble on a house that was falling apart at the seams, but it turned out to be the best investment I ever made

  • No one in my family wanted to move to an inherited home on Chicago’s South Side, but I went for it.
  • It took a lot to fix it up, but the paid-off house meant I could get out of debt fast.
  • I also got to homeschool my kids and make money as a landlord — and I live in a community I love.

When most people think about leveling up financially, they probably don’t envision moving to an under-resourced community, let alone putting down roots and investing there. But that’s exactly what I did, and it was one of the best investing — and personal — decisions I’ve ever made. 

Unlike an absentee landlord visiting the city on weekends to check up on a property, I actually had a financial incentive to relocate there: debt. Like most people of my generation, I was drowning in student loan debt, then added a car note, credit cards, and other miscellaneous debt to my personal balance sheet. Once I got married, my debt grew to a whopping $120,000. 

Getting out of debt was priority No. 1

One of the main reasons I moved to the South Side of Chicago was to get ahead financially. A family member of mine inherited a home there, and no one else wanted to live there (including me at first). But then I realized that taking on a home with no mortgage and not having to pay rent could be the financial break I needed.

Making the leap to move was scary. There were bullet holes in the back door when I got there. Friends and family members thought I was making a bad decision. After all, I had two small children to think about. Everything pointed to this being a very bad idea. 

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Moving to the South Side turned out to be great for our family

Accepting the home was only the first step on my path of “enlightened investing.” The house required quite a bit of clean up and renovating to make it comfortable for my young family. The improvements were tough with a limited budget, along with constant threats of theft and vandalism. There were times the house was broken into and vandalized, but I stayed. 

Once I got settled in with my family, I found, surprisingly, that it was not terrible. I began to enjoy my neighbors and fixing up my home. For the first time, I felt like I was part of a community. We all worked together to make it a livable place for our families. 

Eventually, I was able to pay off all my debt because I had almost no housing expenses. I was even able to homeschool my kids and get them going with acting and entertainment careers. We took classes to learn how to invest their money, and now they will have savings as a launchpad for their life endeavors. 

In the midst of all of this, we were able to volunteer at local organizations and participate in community activities. I sat on nonprofit boards while my kids learned skills like urban farming and 3D printing at these local nonprofits.

Some investing returns are more than dollars and cents. Thankfully, this investment turned out to be good for both my soul and my pocketbook!

I started renting out rooms and turned a profit

At some point, I started renting out rooms in this house. Students, travelers, and community helpers came to our home regularly. I almost couldn’t believe I was making money this way. Surely, this had to be some type of fluke. 

Then, I purchased another property nearby. It also needed renovations, but the rent money I was collecting from the first home helped cover the rehab. Once the renovations were complete, I started renting this property out on a short-term basis, too. It worked again! 

Now, I am looking for another property in the area and am convinced that I could continue replicating this model in the same community. Though the community is still in transition, I’ve proven, time and time again, that there are people who want to pay to both visit and live here. I think it’s a wonderful way to introduce people to the lesser-known parts of Chicago, like my South Side community. 

Why this was a great investment

Aside from the returns and extra income, this investment was a godsend. Even before I collected one red cent in rent, my inner-city home helped me do things that I consider highly valuable to my life: paying off debt, being a stay-at-home mom, and plugging into a community. 

Once I started making money, first by renting out rooms, then by renting out homes, I began to build confidence in my ability to scout out good deals and flip them into profitable investments. Working with contractors, picking out decor, and even selling a home has been a great learning experience. 

Overall, I am still very happy with the choice I made. It was an unlikely success that made money but also taught me many life lessons I would not have learned anywhere else. Until this day, I look at real estate and other investment opportunities somewhat differently. In addition to, “How much can I make?” I am also asking:

  • How much can I learn? 
  • How much can I grow?
  • Who can I help?
  • How will my life change?

The next time you are confronted with what might look like an undesirable investing opportunity, stop and think about returns that are beyond money. You might be surprised at how you can profit and how much you can learn. 

I know that moving and investing in the South Side of Chicago did that for me. May you also find investing decisions that are smart, profitable, and life-changing.

Disclosure: This post is brought to you by the Personal Finance Insider team. We occasionally highlight financial products and services that can help you make smarter decisions with your money. We do not give investment advice or encourage you to adopt a certain investment strategy. What you decide to do with your money is up to you. If you take action based on one of our recommendations, we get a small share of the revenue from our commerce partners. This does not influence whether we feature a financial product or service. We operate independently from our advertising sales team.

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