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Afford Anything | Make Smart Money Choices

Q&A: Should I Sell One Property to Pay Off Another?

Afford Anything | Make Smart Money Choices

Paula Pant | Cumulus Podcast Network

Business, Investing, Entrepreneurship

4.73.6K Ratings

🗓️ 12 May 2026

⏱️ 55 minutes

🧾️ Download transcript

Summary

#714: When you’re making big financial decisions, what matters more: optimizing for the best long-term outcome, or choosing the path that gives you the most flexibility and peace of mind right now? Melissa retired early and now lives off rental income, but she’s considering selling one property to pay off another. The catch? Her monthly income would stay about the same—so the real question is whether giving up future appreciation is worth the simplicity and stability today. Von is trying to better understand how real estate returns actually work—specifically, whether cap rates tell the full story for multifamily properties, or whether there’s more going on beneath the surface. Layla is planning to retire at 50 and has built a strong portfolio—but she’s wondering if she’s leaned too heavily into Roth accounts. Should she keep maximizing a mega backdoor Roth at a high tax rate, or shift toward a taxable brokerage to better bridge the early retirement years? We’ll get into all of that—the tradeoffs, the assumptions behind them, and how to think through each decision. Share this episode with a friend, colleagues, and your Uber driver: https://affordanything.com/episode714 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

Joe, your son invest in rental properties. He does. How many does he have now? He still owns 14,

0:06.9

but he does it also as a full-time job flipping, which, as you know, is a full-time job. That's why we

0:12.9

don't recommend a lot of people do it because of the fact that it is a job. So he's holding on to 14.

0:18.7

He flips a couple at a time and makes a good living out of it.

0:21.9

That's amazing. Well, we are going to hear from someone who, like me, has seven units,

0:27.1

but she's thinking about cutting them in half. Oh, wait a minute. Then she'd only have seven half units?

0:33.7

Well, I guess, I guess technically she would have three and a half units.

0:37.4

Oh, gosh. It's like I never stay when people say would have three and a half units. Oh, gosh.

0:38.7

It's like I never stay when people say they have, you know, the average American has two and a half kids. You're like, oh, I feel bad for the half kid. Right. Or, you know, two and a half bathrooms. I mean, I guess like a half bathroom is a thing, but it's always been. I get the half bath. Right? I don't, I still don't quite get that.

0:54.7

I understand what it means, but it just sounds like funny terminology. A half of a bath. I know this one kid who lost his whole left side and now he's all right. Oh, okay. Let's go. Let's cut to the intro. Welcome to the Afford Anything podcast, the show that knows you can afford anything, not everything. This show covers five pillars. Financial Psychology, increasing your income, investing real estate and entrepreneurship. It's double eye fire. I'm your host, Paula Pant, and the guy crack in lame jokes is a former financial planner, believe it or not.

1:28.3

Someone let this guy be a financial planner.

1:30.6

Joe Sal C-Scihai.

1:32.2

I'm so proud of myself because just when you thought they couldn't get dumber.

1:36.8

You go do something like this and totally redeem yourself.

1:41.1

I'm so proud.

1:43.1

And we're going to cut to our first question, which comes from Melissa.

1:49.4

Hi, Paula and Joe. I would love your help thinking through a decision I'm grappling with on if I

1:53.9

should continue to hold a long-term rental or sell it. I was able to retire early about six years ago

1:58.7

at the age of 49, partially with the great advice I've gotten from this show. I've been supporting myself through the cash flow of three

2:04.7

rental properties and living a dream life pursuing traveling and new interests. My goal has been to

2:10.2

hold them and live off their rents until about the age of 60, which is five years from now, and then

2:14.6

sell them and invest the equity and live off of that plus my retirement

...

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