Episode 738
Property Management, Permits & Profits in Chicago | Michael Root
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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