Ryan Smith, top producing agent specializing in REO properties, returns to provide an update on the state of the Chicagoland foreclosure market heading into 2026!

Ryan starts with an overview on the foreclosure process and expectations when getting into a foreclosure transaction as a buyer. He provides tips on positioning yourself as a legit, experienced buyer in the eyes of REO listing agents. Ryan gets granular on latest foreclosure statistics and provides his outlook on the REO market heading into 2026. He closes with his take on Chicago's crime problem and the neighborhoods that he is bullish on!

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

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

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Guest: Ryan Smith, RE/MAX Properties

Link: Ryan's Instagram

Link: SUCI Ep 70 - Ryan Smith

Link: SUCI Ep 28 - Ryan Smith

Link: The Chicago Way (Podcast)

Link: DAWGS Vacant Property Security

Guest Questions:

02:05 Housing Provider Tip - Understand manufacturer warranties on appliances and reconsider extended warranties!

04:15 Intro to our guest, Ryan Smith!

10:47 Risks associated with buying properties at the auction.

13:12 Understanding properties in receivership.

15:55 Expectations on REO transactions!

25:15 Key Foreclosure Statistics!

35:54 Ryan's outlook on the foreclosure market.

42:55 Promising south and west side neighborhoods.

46:19 Solving Chicago's largest issues.

47:20 What is your competitive advantage?

48:12 One piece of advice for new investors.

49:20 What do you do for fun?

49:50 Good book, podcast, or self development activity that you would recommend?

50:45 Local Network Recommendation?

51:51 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 2026.

Jonathan Klemm of Quality Builders returns to discuss refinements in his General Contracting business and investment strategy since his last appearance!

Jonathan starts by explaining partnership pitfalls to avoid based on recent changes within his business. He gets vulnerable by discussing a multifamily investment on Chicago's southside that involved various evictions and a $400,000 fire caused by a problem tenant! Jonathan shares tips on the mindset required to weather business storms and turns to more positive news by discussing some large renovation projects that his company is working on. He closes with how he has leveraged networking to skyrocket his business and shares his plans for continued growth going into the new year!

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

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Guest: Jonathan Klemm of Quality Builders

Link: Founders (Podcast Recommendation)

Link: SUCI Ep 250 - Jonathan Klemm

Link: SUCI Ep 206 - Prashanth Mahakali

Guest Questions:

02:07 Housing Provider Tip - Perform adequate due diligence specifically as snowy conditions are present!

03:44 Intro to our guest, Jonathan Klemm!

06:50 Partnership pitfalls to watch out for.

15:10 Jonathan's scary "fire" deal!

29:41 Mindset for getting through a difficult deal.

42:41 Large renovation projects by Quality Builders.

48:26 Leveraging BiggerPockets to grow a business.

50:36 Jonathan's 5 Year Outlook!

53:20 What is your competitive advantage?

54:00 One piece of advice for new investors.

54:31 What do you do for fun?

54:38 Good book, podcast, or self development activity that you would recommend?

55:32 Local Network Recommendation?

56:51 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.

Is now a good time for me to purchase in Chicago?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Mark Ainley, Straight Up Chicago Investor Podcast

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

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.