Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

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Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

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Sebastian Mysliwiec, founder of The Dream Rentals, explains how he's built a short-term and mid-term rental management company that delivers top guest experiences and maximizes profits!

Sebastian talks about cutting his teeth and eventually thriving at a marketing company that helped build his real estate skill set. He provides tactical advice on underwriting, marketing, and managing short-term rentals (STRs). Sebastian explains how his team manages seasonality, shares a STR horror story, and top amenities for guests. He closes with remarks on refinancing considerations for STR properties and his team's growth strategy.

If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content!

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guests: Sebastian Mysliwiec, The Dream Rentals

Link: The Dream Rentals Instagram

Link: Skyscraper Tom's Instagram

Link: The 12 Week Year (Book Recommendation)

Guest Questions

01:58 Housing Provider Tip - Leverage Freedom of Information Act (FOIA) to request property info during due diligence!

04:25 Intro to our guest, Sebastian Mysliwiec!

08:31 Defining AirBnB arbitrage.

13:28 Underwriting basics of short-term rentals (STRs)!

20:10 Listing platforms for STRs.

26:09 Managing STR seasonality in Chicago to optimize profit.

35:36 STR Marketing Tips!

45:45 AirBnB Horror Story!

47:46 Top STR amenities.

49:23 Mid-Term Rental analysis and expanding to other markets!

55:13 Refinancing STR properties.

56:47 What is your competitive advantage?

57:15 One piece of advice for new investors.

57:42 What do you do for fun?

58:25. Good book, podcast, or self development activity that you would recommend?

58:54 Local Network Recommendation?

59:29 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec

Straight Up Chicago Investor

Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec