Gil Villegas is the alderperson of Chicago's 36th ward and has focused on generating opportunities for economic and business development to best serve the constituents of his ward!

Alderman Villegas starts by discussing how zoning changes can be utilized to create win-win situations for investors and members of a community or ward! He talks about how he and his fellow members of City Counsel were able to influence the city's approved budget with the needs of their constituents at the forefront. Alderman Villegas breaks down why he chose to withdraw his Ward from the Northwest Housing Ordinance. He closes with an extremely bullish outlook on Chicago leaving us motivated to continue doubling down on our great city!

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: Alderman Gil Villegas, City of Chicago's 36th Ward

Link: Alderman Villegas' Facebook

Link: Alderman Villegas' Instagram

Link: The 48 Laws of Power (Book Recommendation)

Link: NBOA Chicago (Network Recommendation)

Guest Questions:

03:31 Housing Provider Tip - Understand lease renewal notices to remain compliant!

05:28 Intro to our guest, Alderman Villegas!

07:19 Zoning changes to create affordable housing.

18:48 City council's involvement with the city's approved budget.

25:45 How Aldermen work together to make positive impacts!

35:05 Drawbacks of the Northwest Housing Ordinance.

43:34 How Aldermen utilize facts and community input to make decisions.

45:39 Exciting developments in the 36th ward!

48:28 Alderman Villegas' outlook on Chicago.

51:41 What is your competitive advantage?

52:11 One piece of advice for new investors.

54:26 What do you do for fun?

55:46 Good book, podcast, or self development activity that you would recommend?

56:08 Local Network Recommendation?

56:31 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.

What are the common mistakes made when handling lease renewals?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Mark Ainley, Straight Up Chicago Investor and GC Realty

Email the Show: StraightUpChicagoInvestor@gmail.com

Link: Build Your Team | Straight Up Chicago Investor Podcast

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 2026.

Zack Limbaugh of the Limbaugh Law Firm returns to dive deep on code violations including top pitfalls to avoid!

Zack starts by explaining the 101 on buying properties with building code violations! He discusses top lending considerations when attempting to finance a property with violations. Zack dives deep on common code violations, how owners get notified, and how to mitigate your risk! Throughout the show, Zack provides insights on handling various code violation scenarios to give you an edge against the competition!

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: Zack Limbaugh, The Limbaugh Law Firm

Link: Zack's LinkedIn

Link: SUCI Ep 333 - Zack Limbaugh

Link: SUCI Ep 79 - Gary Davidson

Link: Essentialism (Book Recommendation)

Guest Questions:

02:35 Housing Provider Tip - Understand the true costs of not allowing pets in your rentals!

04:44 Intro to our guest, Zach Limbaugh!

10:23 Buying a property with code violations.

16:48 Lending considerations for violations exist.

23:52 Protecting yourself against fines for code violations!

31:03 Ensuring violations are found during due diligence.

43:15 Common violation tickets to watch out for!

50:35 Crazy code violation stories!

51:17 What is your competitive advantage?

51:32 One piece of advice for new investors.

51:39 What do you do for fun?

51:51 Good book, podcast, or self development activity that you would recommend?

52:03 Local Network Recommendation?

52:18 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 2026.

Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career!

Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to create equity! Zach gives property management insights for house hackers which are centered around doing right by tenants and people in general. He explains the ins and outs of acquiring a property by assuming a VA loan. Throughout the episode, Zach demonstrates that growing a portfolio as a busy professional is doable and that the financial reward far outweighs the work that is required!

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: Zach Posey, Chicago Multifamily Club

Link: Chicago Multifamily Club Meetup

Link: Wisdom Takes Work (Book Recommendation)

Link: SUCI Ep 52 - Aaron Zimmerman

Link: SUCI Ep 326 - RJ de Leon

Guest Questions:

01:58 Housing Provider Tip - Understand easy fixes for malfunctioning garbage disposals!

03:57 Intro to our guest, Zach Posey!

07:38 Starting off with a 4-unit house hack.

17:25 Acquiring a second house hack in Roscoe Village.

26:28 Property Management tips for house hackers!

28:44 Leveraging assumable loans to make the numbers pencil.

34:41 The value of networking events.

37:40 Zach's REI goals and outlook on Chicago!

42:42 What is your competitive advantage?

43:13 One piece of advice for new investors.

43:35 What do you do for fun?

43:50 Good book, podcast, or self development activity that you would recommend?

44:40 Local Network Recommendation?

45:39 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.

What is real estate professional status and why is it important for investors?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Michael Procaccio, Pro Financial Services Group Inc

Email the Show: StraightUpChicagoInvestor@gmail.com

Link: Build Your Team | Straight Up Chicago Investor Podcast

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

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Darryl Jacobs, partner at Ginsberg Jacobs, has over 3 decades of experience in tax and corporate law with a focus on tax credit financing transactions.

Darryl starts off with a high-level overview of the various tax credits available to investors. He dives deep on opportunity zones and how geographical areas get designated as opportunity zones. Darryl explains how investors can leverage New Markets Tax Credits. Throughout the show, Darryl demonstrates his deep knowledge in Tax Credits and conveys how it can be a super powerful tool for investors who know how to leverage it!

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: Darryl Jacobs, Ginsberg Jacobs

Link: Sonny Ginsberg (Network Referral)

Link: SUCI Ep 26 - Neal Bawa

Guest Questions:

01:49 Housing Provider Tip - Ensure proper transfer of utilities when purchasing a property to avoid outages!

04:09 Intro to our guest, Darryl Jacobs!

13:26 Understanding Opportunity Zones.

25:04 Opportunity Zones 1.0 vs 2.0!

32:14 New Markets Tax Credits.

54:48 Other tax credit resources for investors.

59:55 What is your competitive advantage?

62:48 One piece of advice for new investors.

64:11 What do you do for fun?

64:37 Good book, podcast, or self development activity that you would recommend?

65:33 Local Network Recommendation?

66:02 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.

What are recent legal updates to the 2026 lease and new squatter laws?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Mark Ainley, Straight Up Chicago Investor Podcast and GC Realty & Development LLC

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

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.