Buying My First Rental Property: A Musician-Turned-Software Engineer’s Journey into Real Estate

Real estate has been on my radar since the summer of 2017 when I studied to become a realtor in Cleveland, Ohio. At the time, I was finishing my music degree at the Cleveland Institute of Music, and I imagined a future where I could balance church music part-time while building a career in real estate. Life took me in a different direction—I became a software engineer—but my passion for real estate never faded.

Fast forward to today, I’ve finally taken the leap and bought my first rental property in Cleveland, a city I know well from my five years of living there while completing my bachelor’s and master’s degrees. Even though I now live in Los Angeles, having family in Cleveland makes it easier to check in on properties and stay connected to the market.

The Biggest Challenge: Finding the Right Property

Buying my first rental wasn’t easy. The biggest challenge was finding a property that met three key criteria:

  1. It had to be in my price range.

  2. It needed to be in decent shape, requiring minimal repairs.

  3. It had to be in a good neighborhood with strong rental demand.

Cleveland offers a lot of affordable properties compared to other major cities, but that doesn’t mean they’re all good investments. I relied on a combination of my personal knowledge of the city and census data to analyze neighborhoods. I also applied financial modeling techniques I learned in my UCLA Extension certificate course in real estate investment analysis to ensure the numbers made sense.

Financing My First Rental Property

Given my strong employment and credit history as a software engineer, I was able to secure a conventional mortgage with 25% down. My goal with real estate investing is to build passive income while continuing to work my W2 job. Software engineering provides stability, but I want to create long-term wealth through rental properties, eventually growing my portfolio to a point where I have financial independence.

One unexpected expense I encountered during this process was home insurance. The insurance companies used the replacement value of the property to determine coverage, and in my case, the replacement cost was extremely inflated. For example, my sub-$200k property was quoted at over $800k to replace. That was a frustrating surprise, and I had to shop around to find a reasonable policy.

The Importance of Tenant Selection

One key lesson I learned early on is that inheriting an occupied property isn’t always ideal. While buying a property with tenants already in place might seem like an advantage, it also means you don’t get to vet those tenants yourself. For my first rental, I wanted as much control as possible over who I’d be renting to.

Since I live in Los Angeles, I’m hiring a property management company to handle tenant screening, rent collection, and maintenance. This will allow me to manage the property remotely while focusing on growing my portfolio.

Long-Term Vision: A Stepping Stone to Bigger Goals

I see this first property as a stepping stone. It may not be the best deal I ever make, but it’s an important first step in my real estate journey. I expect to learn a lot—both from mistakes and successes—and use that knowledge to refine my strategy for future investments.

My ultimate goal is to generate both cash flow and appreciation. If interest rates drop in the future, I plan to refinance to improve my cash flow and reinvest in more properties. For now, I’m focused on making this first deal a success, learning as much as possible, and setting the foundation for long-term financial growth.

Final Thoughts

Buying my first rental property was a major milestone, but it’s just the beginning. Real estate, much like music and software engineering, requires persistence, discipline, and a willingness to play the long game. Whether it’s practicing an instrument for years before mastering a piece, writing code that won’t be used until months later, or investing in a property that will pay off over time, the core principle is the same: consistent effort leads to success.

This journey has been both exciting and challenging, and I look forward to sharing more lessons along the way. If you’re thinking about getting into real estate, my biggest advice is to do your homework, stay patient, and just take that first step.

Garrett John Law

I’m a digital strategist, software engineer, real estate investor, and musician with a deep passion for helping real estate and music industry professionals grow their businesses through smart digital solutions.

I bring a unique blend of technical expertise and industry insight to create solutions that help businesses automate processes, increase online visibility, and generate leads—so you can focus on what you do best.

https://garrettjohnlaw.com
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2025: The Year of My First Investment Property