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 managementHow in-house contracting saves time & money vs outside vendorsThe efficiency of paying by the day vs per projectChicago’s red tape & permitting process compared to suburbsThe value of mid-market multifamily (9–12 units) alongside 60+ unit developmentsTwo types of value-add strategies: heavy vs light renovationsWhy Cook County property taxes are the biggest challenge in underwriting dealsTechnology adoption in property management & leasing tools like ShowMojo📌 Learn more at RootPG.com💡 Want help scaling your real estate business with AI and automation?Schedule your free strategy session today: https://realdealcrew.comCall to Action:Learn more at https://realdealcrew.comTimestamps00:00 – Intro to Michael Root & Root Property Group01:00 – From family business to multifamily investor02:00 – Biggest challenge: clear communication in property management03:00 – Why they brought contracting in-house05:00 – Cost savings by paying crews daily06:00 – Chicago market conditions & pricing challenges07:00 – Target acquisitions: 9–12 units + ground-up 60 units08:00 – Navigating Chicago’s red tape vs suburban permitting09:00 – Technology adoption & efficiency tools11:00 – RootPG’s buy box explained12:00 – Value-add strategies: heavy vs light renovations14:00 – Material choices & design trends over time15:00 – Market challenges: Cook County property taxes16:00 – Why Chicago remains a strong market if you know how to operate17:00 – Rapid fire: lies, advice, books & tools#RealEstateInvesting #MultifamilyInvesting #PropertyManagement #ChicagoRealEstate #ValueAddInvesting #PassiveIncome #RealDealChat #MichaelRoot #RootPropertyGroup #ForcedAppreciation #GeneralContracting #RealEstateOperations #RealEstateTechnology #ApartmentInvesting #CashFlowInvestingRealDealCrew.comWe empower real estate investors by optimizing your business processes through customized automation and system integration. From lead management to deal closure, we help you build a scalable and efficient operation. Learn more at RealDealCrew.comLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramSUPPORT THE SHOW!If you are new to Wealthfront, and open a Cash Account, you'll get a 0.50% APY boost for 3 months.Open an Automated Index Investing Account or Automated Bond Portfolio, you'll earn $5,000 managed for free.Get $10 and Reduce Your Business Costs by Shopping at AppSumo • https://bit.ly/reiappsumoGet $10 Towards Your First Purchase at Drop • https://drop.com/?referer=3DC729