Michael Root shares how he builds value in Chicago multifamily, streamlines property management, and uses in-house contracting to boost efficiency.

In this episode of RealDealChat, Jack sits down with Michael Root, co-founder of Root Property Group (RootPG.com), to discuss property management, multifamily acquisitions, and why Chicago remains both a challenging and rewarding market.

Michael shares how his team handles everything from general contracting to property management in-house, which helps reduce costs, improve communication, and streamline renovations.

Key takeaways from this conversation include:

• Why clear communication is the #1 challenge in property management
• How in-house contracting saves time & money vs outside vendors
• The efficiency of paying by the day vs per project
• Chicago’s red tape & permitting process compared to suburbs
• The value of mid-market multifamily (9–12 units) alongside 60+ unit developments
• Two types of value-add strategies: heavy vs light renovations
• Why Cook County property taxes are the biggest challenge in underwriting deals
• Technology adoption in property management & leasing tools like ShowMojo

📌 Learn more at RootPG.com

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Timestamps

00:00 – Intro to Michael Root & Root Property Group

01:00 – From family business to multifamily investor

02:00 – Biggest challenge: clear communication in property management

03:00 – Why they brought contracting in-house

05:00 – Cost savings by paying crews daily

06:00 – Chicago market conditions & pricing challenges

07:00 – Target acquisitions: 9–12 units + ground-up 60 units

08:00 – Navigating Chicago’s red tape vs suburban permitting

09:00 – Technology adoption & efficiency tools

11:00 – RootPG’s buy box explained

12:00 – Value-add strategies: heavy vs light renovations

14:00 – Material choices & design trends over time

15:00 – Market challenges: Cook County property taxes

16:00 – Why Chicago remains a strong market if you know how to operate

17:00 – Rapid fire: lies, advice, books & tools

#RealEstateInvesting #MultifamilyInvesting #PropertyManagement #ChicagoRealEstate #ValueAddInvesting #PassiveIncome #RealDealChat #MichaelRoot #RootPropertyGroup #ForcedAppreciation #GeneralContracting #RealEstateOperations #RealEstateTechnology #ApartmentInvesting #CashFlowInvesting

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