Bri Conn, CFP®: Welcome to Childfree Life by Design. Today we’re talking about rental properties and what it means for people who are building a Childfree life on their own terms. I’m Bri Conn here with Justin Brown-Woods, and in this episode we’re covering Justin’s story of rental properties, including how he got started, how it went, and how he got out. If you’ve ever wondered if rental properties are as easy as someone makes them out to be, this conversation will give you the clarity and tools to make intentional decisions that support the life you want.
Intro: From Childfree Insights, this is Childfree Life By Design, the go-to resource for building the Childfree life you want. Every episode gives you practical guidance, clear direction, and meaningful conversations to help you live intentionally and design a future on your terms. This podcast is for educational and entertainment purposes only. Please consult your advisor before implementing any ideas heard on this podcast.
Bri Conn, CFP®: All right, Justin Brown-Woods is an accredited financial counselor and co-founder of Price of Avocado Toast with his wonderful wife, Haley. He helps people ditch shame, embrace mindful spending, and build a sustainable financial life aligned with their values. Justin, welcome to the show today.
Justin Brown-Woods: Thanks so much for having me. I’m stoked to be here.
Bri Conn, CFP®: I have been following Price of Avocado Toast since 2020. As I was thinking about rental properties, I wanted to have someone share their actual story—one where situations don’t go as easy as people make them out to be online. Tell us how you even got started in rental properties.
Justin Brown-Woods: It’s a natural progression for a lot of people post-debt. My wife and I wanted to consider what long-term wealth was going to look like. She had family history with rentals, and we realized this might be a decent “passive enough” thing. But we live in Northern California where prices are wild. I started researching on blogs like BiggerPockets and eventually landed on investing in Michigan—specifically a ring city around Detroit called Warren—because the numbers lined up.
Bri Conn, CFP®: So you did this long-distance. How did you pick Michigan?
Justin Brown-Woods: It’s such a stupid story. I’m a high school football coach and I heard a speaker from Michigan talk about the family atmosphere and the students there. Then, when I looked at a forum for the “top booming places,” Detroit ring cities were mentioned. I just decided to look there all because I listened to some football coach years ago.
Bri Conn, CFP®: That’s really funny. So, once you picked the city, how did you find the property?
Justin Brown-Woods: The classic millennial trope: Zillow. In conjunction with BiggerPockets forums, I found a young realtor who was also an investor. He had the same name as my dad, so I decided he was probably safe! He was our first “boots on the ground” in Michigan. He did video walkthroughs, but we never saw the property in person.
Bri Conn, CFP®: You’ve never been to Michigan, even to this day?
Justin Brown-Woods: No ma’am. We also picked Michigan because we wanted somewhere tenant-friendly with a high ethical bar. We didn’t want to be slumlords.
Bri Conn, CFP®: So you virtually got the keys. Talk me through that and the property manager experience.
Justin Brown-Woods: We used a property manager from the realtor’s network. We purchased the home for $92,500 with a mortgage of about $350 a month (taxes and insurance included). In Michigan, you need five different inspections for rentals: plumbing, HVAC, electrical, building, etc. You can’t do them all at once. Because it was post-COVID 2021, the timeline was delayed.
We were a small fish to the property manager. Our $1,400 rent only netted them maybe $140 a month. Inspections kept failing. I remember getting a call at lunch about an $8,000 sewer pipe fix. We were dumping money into a vacant house for a full year. None of the inspections passed, and I realized something was wrong.
Bri Conn, CFP®: A year of paying for an empty house across the country plus repairs. What happened next?
Justin Brown-Woods: We met another investor, Tom Brickman (The Frugal Gay), at FinCon. He helped us as a coach to get out of the property. He actually drove from his properties in Ohio to check ours in Michigan. He told me, “Your neighborhood is nice, but two streets over is a train wreck.” He actually uses dating apps like Tinder when he scouts properties to check the “vibe” of the people in the area!
Bri Conn, CFP®: He’s swiping through Tinder for market research?
Justin Brown-Woods: Yes! He connected us with a different realtor. We eventually sold it for $97,000. We sold it for more than we paid, but after all the rehab and expenses, we were about negative $25,000.
Bri Conn, CFP®: So you exited Michigan. But then there was a second phase?
Justin Brown-Woods: We’re gluttons for punishment. Tom suggested Toledo, Ohio. It was more investor-friendly. We found a duplex owned by a 90-year-old woman. We bought it off-market for $33,000 total—both sides already rented. It seemed like a screaming deal. I paid less for that duplex than most people pay for a car.
Bri Conn, CFP®: What went wrong with the $33,000 duplex?
Justin Brown-Woods: We inherited the tenants. Within three days, the upstairs tenant called me to introduce himself—and apologized for being late because he had been in jail. I looked up the records; he was in jail for domestic violence against his girlfriend, who was the sister of the downstairs tenant. It was an absolute nightmare.
By 2024, the upstairs tenant was ducking rent constantly. We hired a property manager in Toledo to handle it. She was tough and handled the eviction, which only takes three weeks in Ohio. But once he was out and we filled it, the downstairs tenant moved out too. Then the new tenants stopped paying. When we evicted the final downstairs tenant, we found out they had stolen all the copper pipes from the unit.
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Justin Brown-Woods: At that point, Hailey reached out to a financial therapist, Rachel Duncan. By the end of the session, they decided it was time to sell and stop being real estate investors. We tried an auction—no bites. Then we listed it traditionally. We found out we had squatters in the vacant units who had broken in through an upstairs window. Our realtor got them out, cleaned it up, and we eventually sold it for $60,000. After all the headaches, we actually walked away about $6,000 up on that one.
Bri Conn, CFP®: Three evictions and one broken lease in one year. That is wild. Looking back, what are the biggest lessons?
Justin Brown-Woods: First: real estate is NOT passive. It takes one HVAC or sewer issue to put you underwater. Second: investing out of state was unwise for us because we couldn’t be active. Third: avoid “shiny object” syndrome. Social media sells real estate as sexy clickbait—guys in Lamborghinis with 200 units. For a small investor, it’s often just a pit.
Bri Conn, CFP®: How many hours did you spend on this?
Justin Brown-Woods: At least an hour a week of active work, but the mental and emotional energy was constant. It strained our relationship. We believed it was the “path to wealth,” but we were stressed and losing sleep over properties in states we hadn’t even visited. The physiological effects of the stress are real.
Bri Conn, CFP®: Any final thoughts for the audience?
Justin Brown-Woods: Don’t fall for “sunk cost.” At any point, you can back out if it’s not working. Have safe, neutral people in your life who can tell you when it’s time to stop dumping money into a pit.
Bri Conn, CFP®: Let’s move to our final segment: The Deliberate Detail. Share something small you do to design an intentional life.
Justin Brown-Woods: Meal planning for family dinner at the table. Growing up, that wasn’t my standard. When we started our debt-free journey, we realized we spent too much on takeout in front of the TV. Now, with three kids, we eat at the table nightly. It costs nothing but time, but the return is the best in the world. It saves money and gives us a “soft landing” for the evening.
Bri Conn, CFP®: Love it. Where can listeners find you?
Justin Brown-Woods: On all social media @PriceOfAvocadoToast. We are a podcast and financial counseling service helping folks budget and pay off debt so they can grow wealth—and maybe skip the real estate investing!
Bri Conn, CFP®: Wonderful. Remember, intentionally choosing to invest in moments of joy is just as important as investing in your future. Until next time, happy designing.
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