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Straight Up Chicago Investor

Straight Up Chicago Investor

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Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? If so, this podcast is for you! We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate. The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.Copyright of Straight Up Chicago Investor 2021. Economía Exito Profesional Finanzas Personales
Episodios
  • Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows

    Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows
    Nov 20 2025

    SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs!

    Mark jumps right in by giving a bit of history on why rental licenses were originally introduced. He gets granular on various village requirements for rentals including smoke detectors, GFCIs, and hot water heaters. Mark explains some hoops you can expect to jump through during Point of Sale inspections and how to expedite the process! He closes by breaking down tax transfer stamps and other transaction fees in the Suburbs so you can accurately factor this into your holding costs!

    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: Mark Ainley of GC Realty & Development

    Link: Mark's Instagram

    Link: The Science of Scaling (Book Recommendation)

    Link: It's How We Play The Game (Book Recommendation)

    Guest Questions:

    03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up!

    03:16 Housing Provider Tip - Understand the updated CARES Act notice requirements!

    04:55 Intro to our guest, Mark Ainley!

    05:48 The history of village requirements for rentals.

    09:17 Considerations when investing in Schaumburg.

    17:27 Insights on permits and associated fees.

    21:38 Navigating point of sale inspections in different villages.

    31:46 What to know about tax transfer stamps!

    35:56 Overview on rental licenses, village inspections, STR licenses, and more!

    39:51 Book recommendations from Mark!

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
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    43 m
  • Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev

    Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev
    Nov 18 2025

    When do I have to have my cost segregation done to ensure it is good for my 2025 taxes?

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Guest: Cost Seg Kev from CSSI

    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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    Link: Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
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    16 m
  • Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons

    Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons
    Nov 13 2025
    Luke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio. Luke kicks things off by sharing how he acquired his first house hack and provides insights on the ADU process that he used to add a third legal unit. He lays out top considerations when converting a basement into a dwelling unit including the top dollar items. Luke talks about getting a 4-unit acquisition to the finish line, despite it involving violations and a difficult seller. Throughout this episode, Luke demonstrates how holding real estate for the long term has built him great wealth and how staying active in the market is the key to success! 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: Luke Helliker Link: Luke Helliker - DocuSign | LinkedIn Link: EUBA Link: SUCI Ep 345 - Joey Turano Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon Link: SUCI Ep 389 - Sebastian Mysliwiec Link: Rich Dad Poor Dad (Book Recommendation) Guest Questions: 03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up! 05:03 Intro to our guest, Luke Helliker! 13:19 Luke's first deal: a 2-unit house hack! 20:18 How to leverage the ADU process. 27:20 Funding an ADU project. 41:09 Navigating investing with your significant other. 43:15 Acquiring a 4-unit building in a competitive market! 58:47 Lessons learned on the 4-unit acquisition. 65:30 Luke's next investment targets. 66:19 What is your competitive advantage? 67:15 One piece of advice for new investors. 67:59 What do you do for fun? 69:19 Good book, podcast, or self development activity that you would recommend? 70:01 Local Network Recommendation? 70:30 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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    1 h y 14 m
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