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Straight Up Chicago Investor Podcast Episode 209: Building A Portfolio With New Construction Rentals, Strs, And Mtrs With Chicago Reia’s Andrew Holmes

Straight Up Chicago Investor Podcast Episode 209: Building A Portfolio With New Construction Rentals, Strs, And Mtrs With Chicago Reia’s Andrew Holmes

Are you intrigued by the potential of short-term, mid-term, and new construction rentals as investment vehicles? In this episode of Straight Up Chicago Investor, we're joined by Andrew Holmes, a seasoned real estate investor who has successfully grown his portfolio using these strategies.

Andrew begins by comparing the current real estate market to the market in 2012 when he first started investing. He provides a fascinating insight into how the landscape has changed and how he has adapted his strategies to continue to find success.

Next, Andrew takes us on a journey to sunny Florida, where he and his team have been working on a new construction development. He shares the challenges and rewards of this type of investment and how it fits into his overall portfolio.

One of the highlights of this episode is Andrew's discussion on how he has been able to significantly increase his cash flow through short-term and mid-term rentals. He explains his conservative approach to underwriting these investments and how this strategy has paid off.

As we wrap up the episode, Andrew shares his thoughts on the current interest rate environment and the opportunities it presents for investors. He also provides a glimpse into the future, outlining his five-year plan for his team and his investments.

This episode is a must-listen for anyone interested in diversifying their real estate investments and learning from a seasoned pro. Andrew's insights and experiences provide a wealth of knowledge for both new and experienced investors. Don't miss out on this opportunity to learn from one of the best in the business!

Watch Straight Up Chicago Investor Podcast Episode 209 in Full Here

Questions We Answer In this Show:

Q. Running the Numbers for Short Term and Midterm Rental in the Suburban Real Estate Market

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Q. Exploring the Benefits of Airbnb Management for Real Estate Investors


  1. Video

Q. Exploring Short-Term and Midterm Rental Strategies in Chicago Suburbs

  1. Video

Show Notes:

  • 03:31 Housing Provider Tip: Utilize pet screening softwares to prevent scammers from getting away with false pet certificates!

  • 06:07 Intro to our guest, Andrew Holmes!

  • 08:45 Differences between the 2012 and 2023 real estate market!

  • 11:25 What has Andrew been working on since he was last on the show in 2021?

  • 17:19 Andrew discusses lessons learned from building new construction homes in Florida!

  • 24:23 Andrew talks about investing in Short Term and Mid Term Rentals!

  • 39:05 How can you tell if a market has a strong demand for STRs or MTRs?

  • 44:40 Andrew talks about interest rates in today’s market!

  • 47:19 What do the next 5 years look like for Andrew and his group?

  • 50:54 What is Andrew's competitive advantage?

  • 51:17 One piece of advice for new investors.

  • 51:34 What do you do for fun?

  • 51:42 Good book, podcast, or self-development activity that you would recommend?

  • 53:07 Local Network Recommendation?

  • 53:59 How can the listeners learn more about you and provide value to you?

Guest Name: Andrew Holmes

Guest Company: Chicago REIA

Guest Link:

Other Links for show notes:

SUCI Ep 50 - Andrew's Last SUCI Episode

SUCI Ep 62 - Farrah Ali

Diaries of a Female Real Estate Investor (Book Recommendation)

Chicago Investor Resources Shared

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