VRS178 – Practical Vacation Rental Investment Part 2 with Michael Hamilton

Do vacation rentals make a good investment?

This is a question you see occasionally cropping up on the investor websites such as Bigger Pockets, and is invariably answered in the negative. The argument is that they are too time-consuming, are way more involved to set up than a traditional residential rental, and don’t have consistent cash-flow. However, there are many vacation rental owners who consider themselves to be investors and see the process in a different way.

Michael Hamilton is one of these. He was my guest on VRS170 when he talked about his properties in San Diego and South Carolina; how he has renovated them to bring the highest return and why Airbnb is his favored platform for marketing. In today’s episode, Michael helps me understand more about the principles of vacation rental investment.

He explains why it’s important to define the type of investor you are before you make your purchasing decision and why you need to start with the end in mind.

Michael offers a detailed 7-point investment plan that covers market knowledge, financial analysis, and how to develop systems to remove yourself from working in the business so you can spend more time ‘on it’.

If you are considering investing for the first time in vacation rental real estate, this is a brief but concise strategic and operational tour through the steps to be successful. And if you are already in the business, and thinking about your next property, you’ll find it equally valuable.

In this episode you’ll hear about:

  • How not to get on over your head
  • Evaluating your money ‘mindset’
  • The ways to look at it in the long term
  • How to find the intimate market knowledge so you can laser focus on location
  • Evaluating cash flow, returns, and upside potential
  • Ways to identify potential investment opportunities
  • The basics of a vacation rental investment plan
  • Reducing and eliminating ‘time for money’ work

Enjoyed this episode? Be sure to listen to Part 1 > VRS170

Zach McKinnis

Once again Michael, great podcast! This truly captured the importance of creating a system dependent vacation rental business and the mindset shift that will have to accompany it. Very thankful to have your friendship and support in my pursuit of building a vacation rental portfolio. I look forward to seeing many wins coming from you in the near future buddy!


    Lots of win’s starting at 5 in the morning and continuing throughout day!

Gary Troy Miller

Great podcast! Lots of actionable information. I look forward to meeting Mike at VRSS17 and mastermind groups to follow? One thing you touched was how to properly assess a property value. This is something I’d like to learn more about in other countries and how to finance deals? Any books or reading material you could recommend?


    Hi Gary, looking forward to meeting you to next week. Financing is a very interesting and exciting topic, especially when you understand the world of creative financing and structuring real estate opportunities (and my feeling is there are many strategies that can be applied abroad). I love books and get a lot of value out of them. Here is a short list off the cuff: Tim Ferris “Four Hour Work Week,” Michael Gerber + Than Merrill “The E Myth Real Estate Investor,” Seth Godin “Permission Marketing,” Thomas Stanley “The Millionaire Next Door,” Verne Harnish “Mastering the Rockerfeller Habits,” Robert Kyosaki “Rich Dad Poor Dad” – Than Merrill – “Building Wealth in Today’s Real Estate Market.” I plan to put a more comprehensive list.

Michael Garner

Another great podcast by Michael Hamilton. Full of insight and experience and willing to share it with others. Michael does a great job of taking so much of the anexiety and unknowns out of the vacation real estate investment process.
A true pro willing to help newcomers. Thank you.

Jan Newman

I can’t find his handout from this show? He mentioned that he would be preparing a handout for an upload to your show notes. I’d love to see it. Thank you!


    Hi Jan, send me an email to mike@live-swell.com – I have the document and can send it directly to you. We just finished our latest property, “Avalon Beach Bungalow OBX” – this property is a great case study to go along with the plan – a property acquired at a discount from fair market value via marketing systems, structured and negociated well, renovated to force the property appreciation + increase rental rates and, lastly, adopted the operational “systems” of prior properties. A simple google search will ID the “Avalon Beach Bungalow OBX” and we will make it available on your site http://www.live-swell.com shortly….


    Jan the download will be made available here shortly, in the meantime we have uploaded it to our website http://www.live-swell.com/investors/ let us know what other topics you are interested in learning about…Thank you!

    Heather Bayer

    Hi Jan. The handout is live in the show notes above. Enjoy.

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