Jessica Erickson, Director of Economic Development for the City of Woodstock, joins us to discuss development news and opportunities in Woodstock, IL!

Jessica starts with her backstory on moving from Denver to Chicagoland and ultimately taking a role in Economic Development for the City of Woodstock. She breaks down Woodstock's downtown redevelopment plan and also speaks to city corridors with development opportunities. Jessica explains "infill" sites, metrics for successful developments, and strategic planning of developments to allow for future adaptive reuse. Throughout the show, Jessica demonstrates a passion for sustainable developments that enhance the quality of life for the residents of Woodstock!

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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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

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Guest: Jessica Erickson, City of Woodstock

Link: Jessica's LinkedIn

Link: Woodstock Comprehensive Plan

Link: The Prof G Pod (Podcast Recommendation)

Link: Heartland Realtor Organization (Network Referral)

Guest Questions:

02:13 Housing Provider Tip - Utilize water shut off valves at vacant properties to prevent issues!

03:52 Intro to our guest, Jessica Erickson!

09:14 Jumping into Economic Development in Woodstock, IL.

16:50 Woodstock's downtown redevelopment plan.

23:44 Breaking down "infill" sites.

25:54 Measuring successful developments.

29:28 Redevelopment opportunities in Woodstock.

31:27 Future-proofing development sites.

38:41 Closing remarks on the upside of Woodstock!

43:12 Woodstock's competitive advantage?

43:39 One piece of advice for new investors.

44:33 What do you do for fun?

44:55 Good book, podcast, or self development activity that you would recommend?

45:48 Local Network Recommendation?

46:16 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.

Do you need a HELOC on your investment property?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Benjamin Stef, NEXA Mortgage

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

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

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!

=============

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

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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: [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: 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 2026.

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: [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

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Alec Greenberg is the Principal of Base 3 Development and has vast experience developing and stabilizing multifamily assets!

Alec explains how he transitioned from the corporate real estate world to a more entrepreneurial position at Base 3 Development. He describes how he "stretched" out of his comfort zone by jumping into a 6-unit gut rehab project off the bat and shares lessons learned! Alec shares insights on large residential development projects including zoning, underwriting, and leasing considerations. He closes with tips on leveraging VAs and off-shore staffing solutions for optimal property management while also providing a bullish outlook on Chicago!

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: Alec Greenberg, Base 3 Development

Link: Staffolio Website

Link: Chicago Cityscape Website

Link: EUBA - NBOA Chicago

Link: SUCI Ep 412 - Luke Helliker

Link: On The Road (Book Recommendation)

Guest Questions:

02:13 Housing Provider Tip - Understand lease changes coming in 2026!

03:13 Intro to our guest, Alec Greenberg!

08:32 Lessons learned from Alec's first gut rehab project.

13:54 Jumping into a 48-unit development.

22:25 Tips for leasing in the off-season.

25:26 Underwriting rules of thumb on large developments.

35:43 Leveraging VAs and other tools for property management.

49:16 Alec's outlook on Chicago!

51:57 What is your competitive advantage?

52:23 One piece of advice for new investors.

52:39 What do you do for fun?

53:02 Good book, podcast, or self development activity that you would recommend?

53:43 Local Network Recommendation?

55:18 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.

SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down everything you need to know about architectural plans and permits in Chicago!

Tom discusses when you need plans and permits for a project and when it's appropriate to engage an architect. He shares the best way to optimize timelines to ensure your plans and permits get approved as fast as possible. Tom discusses lessons learned on design and functionality particularly on luxury redevelopments! He closes with insights on dormer additions and considerations for ADUs and historic district remodels that will add to your permit approval timeline!

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: Tom Shallcross, Straight Up Chicago Investor

Link: SUCI Ep 235 - Tom Shallcross

Guest Questions:

02:32 Housing Provider Tip - Understand 2026 leasing law changes regarding minors on leases!

04:33 Intro to our guest, Tom Shallcross!

05:35 The process of developing plans and permitting.

14:11 Top design and functionality mistakes!

16:16 Must-have amenities in luxury remodels.

20:40 Timeline for creation of architectural drawings.

27:23 The role of expeditors.

35:29 Design considerations for dormer additions.

41:40 What do you do for fun?

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

How do I navigate the rent determination process for Section 8 applicants in Chicagoland?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Mark Ainley, Straight Up Chicago Investor Podcast

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

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Zeke McDonald-Lewis is an attorney at Erwin Law who specializes in real estate evictions and civil litigation!

Zeke starts by breaking down the first steps in handling a non-paying tenant including the appropriate steps for delivering a 5-day notice. He gets granular on the eviction process timeline and dos/don'ts to avoid delaying the process. Zeke shares top mistakes made in eviction cases and shares horror stories caused by those mistakes! He closes best practices to handle squatters and an outlook on potential changes to the eviction process.

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: Zeke McDonald-Lewis, Erwin Law

Link: Zeke's LinkedIn

Link: SUCI Ep 330 - James Erwin

Link: Red Rising (Book Recommendation)

Guest Questions:

03:50 Housing Provider Tip - Plan tenant payment plans to clear balances quickly!

05:51 Intro to our guest, Zeke McDonald-Lewis!

12:25 First step in dealing with a non-paying tenant.

19:54 Next steps after serving a 5-day notice.

34:18 Timelines for the eviction process.

38:36 Top eviction mistakes.

44:43 Eviction horror stories!

47:25 Dealing with squatters.

51:01 Zeke's outlook on the eviction process!

55:02 What is your competitive advantage?

55:54 One piece of advice for new investors.

56:31 What do you do for fun?

56:59 Good book, podcast, or self development activity that you would recommend?

57:15 Local Network Recommendation?

58:00 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.

Niko Apostal, founder of Niko Collaborative and managing broker at Essex 312, joins us to share his expertise in real estate brokerage with a focus on 2-4 unit buildings!

Niko starts by explaining how he got his real estate business off the ground in the early 2000s and survived the real estate crash! He provides practical tips for anyone looking to start a real estate business. Niko shares details on his first 2-unit building in Logan Square and dives deep into top "gotchas" when purchasing 2-4 unit buildings. He closes with a bullish outlook on Chicago particularly the areas surrounding the United Center!

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: Niko Apostal, Niko Collaborative - Essex 312

Link: The ONE Thing Podcast

Link: The Power of Full Engagement (Book Recommendation)

Link: SUCI Ep 112 - Chicago Cityscape

Guest Questions:

01:58 Housing Provider Tip - Be sure to appeal property taxes particularly with upcoming reassessments!

03:36 Intro to our guest, Niko Apostal!

08:41 Weathering the storm of the real estate crash!

20:53 Lessons learned and tips for starting a real estate brokerage.

30:25 Investing in a 2-unit in Logan Square.

42:00 Essex 312 vs Essex Realty Group.

48:50 Gotchas when buying a 2-4 unit building!

52:10 Neighborhoods that Niko is bullish on!

60:20 5 Year Outlook on Chicago.

62:24 What is your competitive advantage?

63:11 One piece of advice for new investors.

63:27 What do you do for fun?

63:39 Good book, podcast, or self development activity that you would recommend?

64:04 Local Network Recommendation?

64:57 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.