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In Episode 76 of the Real Life Planning Podcast, Cynthia Meyer, CFA®, CFP®, ChFC®, talks with attorney and real estate investor Jen Sperling about the ins and outs of turning a former primary residence into a rental property. Jen shares her experience of doing this not once — but twice — and offers hard-earned lessons and practical advice for anyone considering the same. From choosing a rental strategy to navigating landlord laws and long-distance management, this episode is packed with real-world wisdom for growing a real estate portfolio while staying grounded in your values.

This week on Real Life Planning Podcast:

💡 What should you document before converting your home into a rental? [00:03:00]

💡 Why Jen chose to rent instead of sell—and how that shaped her wealth journey [00:04:05]

💡 What laws, rules, and financial steps must you review before renting your home? [00:06:17]

💡What are the biggest differences between managing condos vs. single-family homes? [00:18:39]

💡How can you align your values with your real estate strategy? [00:25:52]

Takeaway Quotes:

"If you’ve lived in the house, you know its quirks—and that knowledge can save you and your tenant a lot of stress." — Jen Sperling

"Not telling your insurance company that your primary residence is now a rental can void your coverage." — Cynthia Meyer

Connect with Jen Sperling:

Connect with Real Life Planning:

About the Real Life Planning Podcast

Hosts Cynthia Meyer and Vekevia Tillman-Jones explore practical steps for real estate investors to build financial freedom and make working for someone else optional.

If you like this video podcast, consider joining Real Life Planning’s Question of the Week where our CERTIFIED FINANCIAL PLANNERs™ and rental property business owners answer the most common questions about real estate financial planning direct to your inbox.

The ReaL Life Planning Podcast is for educational purposes only. None of the information discussed is intended as investment, tax, accounting, or legal advice, nor as an offer or solicitation of an offer to buy or sell, or as an endorsement of any company, security, fund, real property, or other securities or non-securities offering.

Real Life Planning, LLC is an Investment Advisor registered with the States of New Jersey, New York, Texas, Virginia, and California. All views, expressions, and opinions included in this communication are subject to change. This communication is not intended as an offer or solicitation to buy, hold or sell any financial instrument or investment advisory services. Any information provided has been obtained from sources considered reliable, but we do not guarantee the accuracy, or completeness of, any description of securities, markets or developments mentioned. Our current disclosure brochure, Form ADV Part 2, is available for your review upon request, and on our website, REALLIFEPLANNING.COM.

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77 episodes