#752: Q&A: I’m Tired of Managing My Rental Property. Should I Sell It?

Nieves asks: I recently quit my job and moved to Madrid, Spain for a year to pursue an MBA. I received a scholarship for the program, but I had to use most of my savings for a €20,000 deposit that will be returned after I complete a six-month internship following the MBA. I also took out a €30,000 loan for living expenses for the next 12 months at an interest rate under 4%.

I’m 30 years old and have around $150,000 in my old 401(k), $50,000 in my Roth IRA, and a duplex in St. Louis, Missouri that I bought in 2021 for $240,000. The mortgage, including taxes and insurance, is about $1,500 a month, and it brings in around $3,100 a month in rent. One of the units is a midterm rental, so I have additional expenses associated with that unit.

I’ve been thinking about selling the property because my tenants have started paying late and the property needs a new roof and a few other repairs. I don’t have enough cash to replace the roof out of pocket, and managing the property from abroad has become stressful. I could likely sell the duplex for around $250,000 to $275,000, and I currently owe $180,000 on the mortgage.

How do you know when it’s okay to let go of an investment that is objectively a good long-term asset? I’m struggling with whether selling would be a smart simplification for peace of mind or if I’d be giving up a valuable long-term asset.

Mandy asks: I really loved your most recent podcast on the July jobs report that came out. I saw something recently in the news stating that 100% of the labor workforce decline was actually female, and that 100% of it was females leaving the workforce. I wasn’t sure how accurate or correct that information was, and I was curious if it is accurate, what is the reason behind it and what factors are impacting that?

James says: Hi Paula, my name is James. I’m calling regarding episode 744 with Joseph Moore, the historian that you had on, and that was one of the most interesting podcasts about finance that I’ve ever listened to. I just wanted to call and give you that accolade and to say that I will keep listening to your show on a regular basis. I’m a full-time stacker and a part-time afforder. So keep up the good work, and I look forward to listening to your episodes in the future. And also make it easier to leave a review on your website because I couldn’t figure out how to do that. So that’s why I’m leaving this message. Talk to you later. Bye.

• Don’t let temporary problems drive permanent decisions: One set of late-paying tenants is a short-term, solvable problem; if you own rentals for decades, you’ll see every kind of tenant. Before you sell rental property, I want to make sure you’re not making the right decision for the wrong reason.
• A new roof is a front-loaded investment: Every major capital expenditure buys years of not having to think about that component again. A roof can last 25 to 30 years, so before you sell rental property over one big repair, remember that your future self benefits from the payment.
• A property manager can solve what selling solves: Deciding to sell rental property gets you away from tenant headaches, but so does hiring a professional. Beyond the time savings, a good manager brings local legal expertise, handles contractors, and gives you real peace of mind, especially if you’re managing from another country.
• Compare unleveraged returns before you sell rental property: Add the property’s cap rate to its expected appreciation, then compare that to what your after-tax, after-fee proceeds could earn elsewhere, like an S&P 500 index fund. Just remember it’s not a risk-adjusted comparison, since every property has its own risk profile.
• A labor force decline isn’t the same as job losses: Labor force participation counts people who have jobs or want them. In many cases, July’s drop reflects women moving from wanting work to not wanting it, driven partly by childcare costs and return-to-office mandates, a multi-year trend among mothers of young children.
• Zoom out before you trust a single month: Women made up 100% of July’s labor force decline, but they also captured 98% of August’s net job growth and about 85% of 2026’s job gains so far. One month makes a headline; the long-term trend line tells the real story.

Episode 744 with Historian Joseph Moore
The episode James called in about, on the long historical view of money and why grounded, data-driven optimism is so hard to find.
Listen to the episode

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Joe’s Interview with Joseph Moore on Stacking Benjamins
Joe asks Joseph Moore a completely different set of questions, and there’s a downloadable cheat sheet with the interview’s top takeaways.
Watch on YouTube

Bureau of Labor Statistics: Employment Situation Report
The BLS jobs data behind our discussion of labor force participation and 2026 job growth.
Read the report

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