Episode 402: Looking At Chicago Investing Differently with Jason Wagner

from Straight Up Chicago Investor · host Mark Ainley and Tom Shallcross

Jason shares why he chose to invest in Chicago's northwest side and how he's achieved success in that area. He breaks down assumable loans and 2-1 buydowns including how these tools can be leveraged to improve an asset's ROI! Jason discusses the power of the data he compiles in the Wagner Report and how investors can utilize it for a competitive edge. He closes with bullish remarks on Arlington Heights and powerful advice for new, aspiring investors! 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] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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: Jason Wagner, Greystone Realty Link: SUCI Ep 224 - Jason Wagner Link: Real Life Investing with Jason & Rachel Wagner (Podcast) Link: Wagner Report Link: The 5 Types of Wealth (Book Recommendation) Link: SUCI Ep 244 - Ryan Bakke Guest Questions 02:36 Housing Provider Tip - Ensure utilities are put back in your name in between tenant turnovers! 04:52 Intro to our guest, Jason Wagner! 10:53 Emerging neighborhoods and creative strategies for cash flow! 28:42 Ins and outs of assumable loans. 36:06 Insights on VA loan assumptions. 38:03 The background on Greystone Realty. 42:56 Housing market takeaways from the Wagner Report! 45:58 Opportunities in Arlington Heights. 50:26 Best of advice for aspiring real estate investors. 52:42 What is your competitive advantage? 53:07 One piece of advice for new investors. 53:20 What do you do for fun? 54:28 Good book, podcast, or self development activity that you would recommend? 56:19 Local Network Recommendation? 57:11 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

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This episode was published on September 25, 2025.

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