From Short-Term to Midterm Rentals: Bailey Kramer on Systems, Stability, and Scaling with Hospitable

Bailey Kramer, a full-time real estate investor and longtime Hospitable user, joins the Hospitable Host podcast to explain his shift from co-hosting up to 30 short-term rentals across multiple markets to primarily owning and operating 10 midterm rental units. He says the main driver was operational burden from frequent STR turnovers, while MTRs run at a slower pace with fewer turnovers and can be managed solo using similar systems. Kramer addresses misconceptions that MTRs are less profitable, noting STR revenue can be higher but often carries heavy turnover-related costs; he highlights utilities as an overlooked MTR expense. He discusses using Hospitable for automated messaging, cleaner coordination, smart lock codes, and managing manual bookings from Furnish Finder and insurance stays, and emphasizes minimum-night settings and a hybrid STR/MTR seasonal approach. He also shares why he launched the Midterm Rental Show and a community to cover MTR-specific nuances, stressing patience and long-term mindset.00:00 Welcome and Episode Setup00:53 Meet Bailey Kramer01:45 From Co Hosting to Ownership02:22 Why Switch to Midterm Rentals03:46 Midterm Profit Misconceptions05:00 Operations at Slower Speed06:28 Using Hospitable for MTRs07:52 Systems That Break First09:16 Hybrid STR to MTR Strategy10:58 Podcast and Community Launch13:50 Scaling Mindset and Patience16:47 Quick Fire Midterm Q and A19:22 Where to Find Bailey20:18 Wrap Up and Subscribe