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

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

#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

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The 5 Ways Investors Behave When Things Go Wrong, with Clare Flynn Levy

The 5 Ways Investors Behave When Things Go Wrong, with Clare Flynn Levy

#717: Clare Flynn Levy was a hedge fund manager in London in the summer of 2007, watching her trading screens turn red — every single day. Merger arbitrage spreads were widening. Investors were pullin...

22 Touko 1h 5min

Q&A: Your Kids Just Inherited $350,000 Each. Now What?

Q&A: Your Kids Just Inherited $350,000 Each. Now What?

#716: When does a financial decision stop being purely about maximizing returns—and start becoming about building the life you actually want? Karen recently inherited sizable trusts for their chi...

19 Touko 1h 13min

Mrs. Dow Jones: Your Childhood Is Running Your Bank Account

Mrs. Dow Jones: Your Childhood Is Running Your Bank Account

#715: She grew up with a Goldman Sachs dad. She still ended up broke in her 20’s. Here's what changed. Haley Sacks - known online as Mrs. Dow Jones - joins us to talk about the five-step financial fr...

15 Touko 1h 9min

BONUS: The Economy Added 115,000 Jobs. Consumer Confidence Just Hit a 74-Year Low. Let’s Unpack This.

BONUS: The Economy Added 115,000 Jobs. Consumer Confidence Just Hit a 74-Year Low. Let’s Unpack This.

The US economy added 115,000 jobs in April -- and the numbers look solid on the surface. But dig a little deeper and you'll find a tech sector in freefall, a housing market frozen in place, and cons...

11 Touko 24min

Why Smart People Still Sabotage Their Own Money, with Tiffany Aliche

Why Smart People Still Sabotage Their Own Money, with Tiffany Aliche

#713: Tiffany Aliche spent her 30th birthday in her childhood bedroom, $300,000 in debt, unemployed, and freshly foreclosed on. 

Sixteen years later, she's generated over $50 million in gross revenue...

8 Touko 1h 14min

The Rental Strategy That Survived Every City Crackdown, with Jeff Hurst

The Rental Strategy That Survived Every City Crackdown, with Jeff Hurst

#712: Jeff Hurst, CEO of Furnished Finder, joins us to break down what midterm rentals are, who they're for, and why now might be the best time to get in. A midterm rental is a furnished unit rented ...

5 Touko 1h 32min

Is a Computer Science Degree Still Worth the Debt?, with Ron Lieber

Is a Computer Science Degree Still Worth the Debt?, with Ron Lieber

#711: A computer science degree used to feel like a sure thing. Job placement rates topped 90 percent. Starting salaries cleared $80,000. You could do the math on your student loans before you enrolle...

1 Touko 1h

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