Mid-Term Rentals EXPOSED: When They Win, When They Fail episode artwork

EPISODE · Feb 23, 2026 · 37 MIN

Mid-Term Rentals EXPOSED: When They Win, When They Fail

from The Rentish Podcast · host Zach and Patrick

Send us Fan MailWe’ve talked about long-term rentals. We’ve talked about Airbnb.But we’ve never talked about this.In this episode of The Rent-ish Podcast, Zach and Patrick welcome Bailey Kramer, the first guest we’ve ever had, to break down mid-term rentals, the in-between strategy most investors either misunderstand or completely ignore.Bailey shares how he started investing while still in college, why he chose mid-term rentals over traditional leasing, and what actually makes this strategy work (and fail). We get into the real numbers, why furnishing matters more than people expect, how tenant screening changes by platform, and why mid-term rentals are not the “safe middle ground” everyone assumes.If you’ve ever wondered whether mid-term rentals are a hidden opportunity or a risky distraction, this episode gives you the honest answer.No hype. No gurus. Just the reality.Check out Bailey's YouTube channel, where he has a plethora of real estate information and tips. HEREhttps://ledgre.ai/?utm_source=Podcast&utm_medium=OrganicSocialMedia&utm_campaign=Feb2026Promotion Learn More https://innago.com/podcast/  https://joincohorts.com/Sponsors: Innago is a free, online property management software designed for landlords, particularly those managing small to medium-sized portfolios. It offers a range of features to simplify tasks like rent collection, lease management, maintenance requests, and tenant screening. Ledgre is an All-in-One Accounting Software Built for Rentals. Organize property transactions, track expenses, and automate rental accounting with simple software focused on your industry.Cohorts where serious real estate leaders level up. Join a curated peer group of founders, principals, and GPs who meet monthly in small, high-value circles. No fluff—just real insights, real accountability, and direct access to people who’ve done it before.Follow us on Instagram 

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Send us Fan Mail We’ve talked about long-term rentals. We’ve talked about Airbnb. But we’ve never talked about this. In this episode of The Rent-ish Podcast, Zach and Patrick welcome Bailey Kramer, the first guest we’ve ever had, to break down mid-term rentals, the in-between strategy most investors either misunderstand or completely ignore. Bailey shares how he started investing while still in college, why he chose mid-term rentals over traditional leasing, and what actually makes this st...

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Mid-Term Rentals EXPOSED: When They Win, When They Fail

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