Money for Life with Eric Roberge, CFP
Money for Life with Eric Roberge, CFP
Eric Roberge, CFP & Beyond Your Hammock
The Inside Track on Becoming a Landlord: Understanding Property Management with Peter Cook
38 minutes Posted Jun 15, 2026 at 9:00 am.
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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 true financial cost (not just an inconvenience)
  • The one-year lease rule that protects both landlords and tenants
  • An insider tool almost no one uses: the tenant handbook.

Peter also breaks down the specific criteria good property managers use to screen tenants, the math on maintenance reserves, and how to actually find a trustworthy property manager if you're not going to do it yourself.

Real estate can absolutely be a strong long-term wealth-building strategy for high earners, but it's not for everyone and works best when you go in with both eyes wide open to the realities. This episode gives you the financial framework and the practical details to make that call clearly.

Peter is the President of Annapolis Property Services. Originally from Wales, Peter moved to Annapolis in 1999 as the General Manager of Sunsail Sailing Vacations. In 2003, after recognizing the need for long-term residential property management in and around the Annapolis area, he founded Annapolis Property Services. Peter is a licensed Real Estate agent, a member of NARPM (National Association of Residential Property Managers) and a graduate of Southampton University. In his spare time he enjoys sailing, Adventure motorcycling, snowboarding and spending time with his family and friends.

Resources mentioned:

  • PropertyManagement.com: Directory of vetted property management companies searchable by zip code
  • NARPM.org: National Association of Residential Property Managers

 

Ready to create, use, and enjoy money for life? Request a complimentary consultation with us at BYH and discover how to optimize your investments, reduce your tax burden, and grow your wealth: https://beyondyourhammock.com/schedule