#330 - Scaling to 10 Rental Units by 25 with Midterm Rentals - Bailey Kramer episode artwork

EPISODE · Jun 10, 2026 · 57 MIN

#330 - Scaling to 10 Rental Units by 25 with Midterm Rentals - Bailey Kramer

from Living Off Rentals · host Kirby Atwell

Joining us in this episode of Living Off Rentals is Bailey Kramer, a 25-year-old real estate investor who built a portfolio of 10 rental units by focusing on mid-term rentals. Bailey shares how he got started in college, why he chose mid-term rentals over traditional Airbnb listings, and how he scaled his business by learning operations, networking with experienced investors, and taking action early. Listen as he breaks down the lessons he learned from running 30 short-term rentals, buying properties remotely, and building a rental business that creates strong cash flow without the constant headaches of nightly turnovers. Enjoy the show! Key Takeaways: [00:00] Introducing Bailey Kramer and his background [02:49] Building rental income while still in college [06:43] Pursuing business and real estate through YouTube University [09:19] The power of networking and joining a real estate mastermind [11:20] Taking action after months of analysis paralysis [15:22] The idea of pursuing midterm rentals [18:28] Managing 30 short-term rentals and the burnout that came with it [25:54] Buying his first property for $115,000 [28:43] Why Bailey prefers midterm rentals over traditional short-term rentals [30:09] The types of tenants that fill his midterm rental properties [36:53] Building systems and teams to manage rentals remotely [38:32] Simple, consistent deals often outperform flashy investments [41:35] Bailey's goal in the business [48:57] What makes a good deal in midterm rentals? [51:37] Ideal cash you must leave in the deal [53:52] Advice for young investors trying to get started in real estate [57:28] Outro Guest Links: Website: https://baileykramer.com/  YouTube: https://www.youtube.com/@baileykramer Instagram: https://www.instagram.com/the_bailey_kramer/ Show Links: Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call Living Off Rentals YouTube Channel – youtube.com/c/LivingOffRentals  Living Off Rentals YouTube Podcast Channel - youtube.com/c/LivingOffRentalsPodcast  Living Off Rentals Facebook Group – facebook.com/groups/livingoffrentals  Living Off Rentals Website – https://www.livingoffrentals.com/  Living Off Rentals Instagram – instagram.com/livingoffrentals  Living Off Rentals TikTok – tiktok.com/@livingoffrentals 

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#330 - Scaling to 10 Rental Units by 25 with Midterm Rentals - Bailey Kramer

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How long is this episode of Living Off Rentals?

This episode is 57 minutes long.

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This episode was published on June 10, 2026.

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Joining us in this episode of Living Off Rentals is Bailey Kramer, a 25-year-old real estate investor who built a portfolio of 10 rental units by focusing on mid-term rentals. Bailey shares how he got started in college, why he chose mid-term...

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