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How to Successfully Invest in Short Term Rentals!

Investing in short term rentals has become immensely popular in the past year(s). And for good reason! Short term rental investing:

  • Is an amazing strategy to accelerate wealth building
  • Allows you to purchase an investment that you can also enjoy yourself
  • Provides incredible tax benefits

However, there is a caveat

You have to invest in short term rentals the right way. And the right way is not always the easy way. I cringe whenever I hear another physician tell me that they are going to buy a short term rental. I always ask them what their expected return is, if they’ve researched local short term rental regulations, and how they plan to manage it.

Almost 100% of the time, they don’t know the answers. Many times, they are rationalizing a reason to buy a vacation home that they cannot afford. This leads to disaster.

Other times, they are genuinely interested in short term rental investing but naive to the work that needs to be done to get to the point where it is more passive. (Remember, there is no true thing as passive income, it’s all really leveraged income.)

Why am I sharing this with you?

The reason is simple. Ian Cook and Lauren Ihde of Carpe Diem MD are opening their Short Term Rental Course up for enrollment again starting September 13, 2021!

And you can now sign up!

Selenid and I took this course in 2020

I consider this course to be mandatory learning if you are interested in short term rentals.

Simply put, it is the most thorough and well prepared online course that I have ever taken. Even compared to some online college courses that I’ve taken.

Ian and Lauren have put together a curriculum that will take you from zero knowledge of short term rentals to buying your first property. They have all of the resources including an incredible STR analysis spreadsheet that takes you step by step through analyzing every aspect of a potential property.

The course also introduces you to fantastic team members like lenders, insurance brokers, asset protection services, and tax experts.

We really cannot recommend this course enough. And the best part is that it includes CME so you can use your CME dollars to pay for it!

So, I want to provide an overview of the course, what it includes, and what you will accomplish by enrolling.

Course overview

The goal of the Carpe Diem MD Short Term Rental course is to guide you through the process of purchasing your first or next Short-Term Rental Property. 

short term rentals

The course will begin with choosing your market and progress to analyzing properties with the goal of completing your purchase. The course will also cover how to set up and manage your Short-Term Rental property including the process of automation. We have done the research to help you stream line your set up.

After completing this course you will be able to join a community of physician STR investors. This community functions as a resource for continued investing, support and Short-Term Rental guests. Members of the CDMD STR community enjoy 18% off of short term rentals bookings at no cost to the host.

As a guest you save 18% on your bookings and as an owner you gain vetted physician guests. Sign up for the course to learn how!

This course is designed for Physicians by Physicians and we understand the stresses you experience in your profession. We know you can do this and can tell you that owning a STR is a great retreat.

It is possible to manage a STR with your schedule.  In addition, you do not need to quit medicine to own and manage STR rental properties. Lastly, you can enjoy the tax benefits usually reserved for REPs via STR ownership.


After your first STR purchase you will have the skills to manage your own property and the ability to add to your portfolio and scale. 

According to Ian and Lauren owning our Short Term Rentals has been one of the best decisions they ever made.  They have made many great memories with family and friends at their property.  The bonus is that the cost of this great vacation home has been covered by short-term rental income.  It has truly been the best of both worlds.


And the first course offering of this year begins January 24, 2022!

Sign up today!

Topics covered in the CDMD STR course

  • The Mindset of Short-Term Rental Ownership
  • What type of Short-Term Rental Investor are you
  • How to analyze your market
  • How to analyze your property
  • Legal structure options
  • Insurance for Short-Term Rentals
  • Financing your Short-Term Rental
  • The Pros and Cons to Property Management vs Self Management
  • Finding an agent to assist you in making your first STR purchase
  • How to list your property on AIRBNB, VRBO,
  • Successfully manage your own property
  • Automate your property management
  • Become comfortable with bookkeeping
  • Develop a process to scale if you want to build a STR portfolio
short term rentals


What is the cost of the course?

The course costs a total of $2,550. This is paid in 3 payments of $850 each.

Is that cost worth it? Well, let’s run the numbers

First, a full disclaimer. I took a real estate course for long term rental/multifamily investing and spent more than the above price. Paying for a course kept me on task and focused. I was not going to waste my education investment. That course was worth the cost and I hope you will have the same experience with the CDMD STR course.

$2,550 is a fraction of your College and Medical School education. At this price point you be introduced to an entirely different field. The course is designed to provide education tailored to Physicians and provide you the tools to invest in STR real estate.

Another way to look at the cost of the course is to analyze your potential returns (we can’t guarantee returns).

If you learn how to purchase cashflowing STRs through this course then you make your education investment worthwhile. For example, a property that cashflows $10,000 a year would result in a 4x return on your education investment.

Tax saving from a $500,000 property could be as high as $50,000 which would be a 20x return on your education. (We discuss how this is possible during the course)

Learning to self manage will save you 10-30% depending on your market. We are saving $8,000 per year (3x return on your education investment)

By joining the CDMD STR Community you will gain high quality referrals and receive 18% discounts on STR bookings.

Lastly, and most importantly, you will have a STR property that you can enjoy with your family and that is PRICELESS.

Bonus: CME!

6 hours of CME will be available via the Physician Burnout and Wellness CME portion of the course. This means that you can take the course and use your CME money to pay for it!!!

The course is now open for January 2022!

Remember, with the course, you will also join the CDMD STR Community of like-minded STR owners and enjoy 18% discounted bookings and referrals from within the community!

As you all know, I only ever recommend services that I have used or vetted extensively. This fits the bill on both ends! I can say very honestly and proudly that this is a fantastic course and one that I recommend to anyone interested in investing in short tern rental properties to accelerate their path to financial freedom!


What do you think? Have you considered investing in real estate? Have you considered short term rentals? What holds you back? Let us know in the comments below!

(This post contains an affiliate link, which means that I receive a fee when you buy using my link at no extra cost to you!)

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    Jordan Frey MD, a plastic surgeon in Buffalo, NY, is one of the fastest-growing physician finance bloggers in the world. See how he went from financially clueless to increasing his net worth by $1M in 1 year and how you can do the same! Feel free to send Jordan a message at [email protected].

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