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July 17, 2025 58 mins

Welcome back to Modern Financial Wellness! In today’s episode, I tackle one of the most pressing and emotionally charged questions in personal finance: Should you rent, or should you strive for homeownership? Rising interest rates, surging home prices, and shifting economic forces have made the decision more complicated than ever. With headlines declaring the “death of the American Dream,” many are left wondering—is owning a home still possible, or even the right choice?

To dig into this topic, I’m joined by repeat guest John Donlon of Gold Coast Mortgage in Beverly, Massachusetts. John brings decades of experience working on the front lines with home buyers, and his practical, thoughtful approach to the renting versus owning debate makes him an invaluable resource for anyone pondering a move.

John and I dove into the emotional, financial, and economic realities facing would-be homeowners and renters today. We discussed the deep-seated fears associated with taking on a mortgage, including the relentless nature of those monthly payments and how life’s unpredictability can make homeownership intimidating. John provided perspective on why these concerns aren’t new but have evolved—especially with the entrance of private equity firms and institutional investors who are reshaping the rental landscape.

We also examined how renting can offer flexibility but is now often managed by detached corporations rather than local landlords, leading to higher rents and less personal interaction. John and I shared stories from our own lives and those of our clients—illustrating the “aha moments” that drive people to take the leap into homeownership (or decide to wait), and how those moments are often driven more by lifestyle and family needs than strictly by finances.

Much of the conversation focused on how to know when you’re really ready for homeownership, the risks of rushing in for the wrong reasons, the myths about timing the housing market, and why waiting for the “perfect” rate or price can backfire. John explained the truth behind mortgage rates, the critical mistake of trying to time the market, the importance of affordability, and the long-term wealth-building aspects of owning a home—even in challenging environments.

5 Key Takeaways

  1. Homeownership Is a Serious, Long-Term Commitment—But It’s Always Been Scary: Taking on a mortgage is intimidating and a huge responsibility. That fear is nothing new; our parents and grandparents felt the same anxiety in their own time, even if their numbers were smaller. The perceived threat is less about the numbers and more about the relentless nature of the obligation.
  2. The Rental Game Has Changed—And It’s Not Always in Your Favor: The rise of private equity and corporate ownership in the rental market means tenants are often dealing with faceless algorithms, not caring landlords. Rents are determined by market-maximizing algorithms rather than people, making it harder for renters and contributing to the rising cost of both renting and buying.
  3. The “Aha Moment” Should Drive the Decision More Than Math Alone: Most people don’t jump into ownership solely for financial reasons. The decision to buy is often triggered by changes in lifestyle—like needing space for family or wanting more stability—rather than doing a simple rent vs. buy calculation. Running toward ownership only for a perceived tax break or “cheap” mortgage rate can lead to regret.
  4. Don’t Try to Time the Market—Your Personal Readiness Matters More: Waiting for the “right” interest rate or a drop in home prices rarely works out. None of us (not even the experts!) can reliably predict mortgage rates or housing prices. Instead, focus on your personal “clock”—your needs, career, and readiness. Honor your own timing rather than market...
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