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 💡 Want help scaling your real estate business with AI and automation? Schedule your free strategy session today: https://realdealcrew.com Call to Action: Learn more at https://realdealcrew.com 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 RealDealCrew.com We 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.com LIKE • SHARE • JOIN • REVIEW Website Apple Podcasts
