Episode 257: The Playbook For Short-Term Rentals in Chicago with Ditron Corker

Ditron is a seasoned Short-Term Rental (STR) Investor who is teaching others how to get started and maximize profitability with STRs.  Ditron shares how he got started in real estate and utilized the house hacking and rent-by-the-room strategy. He shares tremendous nuggets on finding good STR markets and typical expenses associated with setting up and running a short-term rental. Ditron gives tips on working with AirBNB, STR expectations, amenities, and FAQs to consider to set yourself up for success. Mid-Term Rentals, STR underwriting, and automation are also discussed on the episode. This show is full of STR jewels of wisdom that you won’t want to miss! If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Guest: Ditron Corker, Roam to Rome Spaces & STR Innovate Link: Ditron's Meetup Link: SUCI Ep 143 - Jessica Ryan Link: Who Not How (Book Recommendation) Link: Jeff Ma and Eli Goodman Meetup ----------------- Guest Questions 03:10 Housing Provider Tip: Deliver a nicely landscaped property to encourage upkeep! 05:37 Intro to our guest, Ditron Corker! 08:00 Ditron’s first deal! 09:20 Getting into short-term rentals (STRs)! 13:46 Expenses on STRs. 20:07 STR-Specific Features and FAQs! 24:27 Entertainment amenities in STRs. 25:56 Where are STRs allowed? 31:08 Underwriting STRs! 35:34 STRs vs MTRs. 38:55 Automation Systems. 40:50 Lessons Learned! 46:06 Tax Advantages to STRs. 49:22 Ditron’s upcoming conference! 51:49 What is Ditron’s competitive advantage? 52:25 One piece of advice for new STR investors. 53:02 What do you do for fun? 53:24 Good book, podcast, or self development activity that you would recommend? 54:05 Local Network Recommendation? 55:14 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.