The Inside Track on Becoming a Landlord: Understanding Property Management with Peter Cook

The Inside Track on Becoming a Landlord: Understanding Property Management with Peter Cook

June 15, 2026 · 39 min · Episode 86

About this episode

Peter Cook joins Eric Roberge to discuss the realities of becoming a landlord and managing rental properties.

Want to get rich and earn passive income? Invest in real estate, baby! Only, it's not that simple, and today's expert guest has a truly inside track to explain why. Today on the show, Annapolis Property Management founder Peter Cook joins us to explain what high-income earners need to understand before they wade into the waters of real estate investing and rental property management. Peter has spent 25 years in property management, and in this episode, he and Eric dig into a real, unfiltered breakdown of what it means to be a landlord. Not the theoretical version from a book or a podcast that romanticizes rental income as the best way to riches — but the operational reality of tenant screening, rent pricing, vacancy costs, maintenance reserves, and the relationship dynamics that determine whether your investment is a wealth-builder or a financial headache. If you already own a property and you're wondering whether to rent it or sell it (especially if you're moving up to a bigger home but aren't ready to let go of your first place) this conversation is for you. You'll hear: Why your mortgage rate is completely irrelevant to what rent you can charge How to think about vacancy as a…

People in this episode

Host: Eric Roberge

Guest: Peter Cook

Mentioned in this episode

Organizations: Annapolis Property Management

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