Episode 479: Finding Cash Flow in Chicago's A Class Neighborhoods with David Shifrin

David Shifrin of Elite Properties Chicago returns to share how he has scaled his portfolio since his last SUCI podcast appearance in 2024! David opens up by summarizing his portfolio and how he created cash flow in premier Chicago neighborhoods! He breaks down how a 1031 exchange works and gets granular with an example that led to the acquisition of a great multifamily asset in Avondale. David shares some lessons learned from a rough rehab project and talks about strategies to raise rents and property value without having to do significant renovation. He closes with his take on current investment opportunities in West Town and a bullish outlook on Chicago as a whole! 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: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement 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 ============= Guest: David Shifrin, Elite Properties Chicago Link: SUCI Ep 280 - David Shifrin Link: David Shifrin's Bio Link: NBOA Chicago Link: Illini Inquirer Podcast Guest Questions: 02:00 Housing Provided Tip - Consider a sump pump system to protect your properties during heavy rain falls! 03:12 Intro to our guest, David Shifrin! 05:40 Finding cash flow in class A neighborhoods. 08:00 Breaking down 1031 exchanges. 11:41 David's recent Avondale multifamily deal! 15:22 Pros and cons of paying down mortgages. 25:14 David's top lessons learned from rapidly building a portfolio. 29:24 Opportunities to be had in West Town. 40:06 David's outlook on Chicago! 44:20 What's your competitive advantage? 44:34 One piece of advice for new investors. 45:00 What do you do for fun? 45:42 Good book, podcast, or self development activity that you would recommend? 46:44 Local Network Recommendation? 47:27 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.