From Landlord to Housing Provider: Navigating Chicago’s Tougher Rental Laws
Welcome to the first episode of The Housing Provider Show, the rebranded podcast for Chicago landlords, property managers, and real estate investors.We’re diving into the challenges housing providers face in 2025:- Why Chicago tenant laws are becoming tougher- New regulations like the Fair Notice Act & 606 Pilot Program- How tenant unions and political pressure are changing the rental landscape- What small landlords and investors can do to protect their business and grow their portfolioWhether you own one rental or manage multiple properties, this episode gives you insights, strategies, and real talk about staying profitable in a city that’s becoming less landlord-friendly.Subscribe now so you don’t miss future episodes with expert guests, Chicago market updates, and actionable tips for housing providers.Got a question for us? Drop it in the comments, we might feature it on the show!
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28:48
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28:48
2025 Illinois Landlord Law Changes You Need to Know
In this episode, Tim Harstead from Chicago Style Management breaks down the key legal changes every Illinois landlord must understand for 2025. From mandatory flood disclosures to updated late fee limits and a streamlined eviction process, Tim explains what’s new, what’s risky, and how to stay compliant. He also dives into the new retaliation law and offers tips on how to legally justify non-renewals and rent increases.Whether you self-manage or work with a property manager, this episode is packed with must-know updates that could save you time, money, and legal trouble.
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11:16
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11:16
Tax Loopholes For Real Estate Investors (save money legally)
Want to save thousands on your rental property taxes? In this episode of The Landlording Show, Tim Harstead reveals the #1 strategy smart real estate investors use to reduce taxes and grow their profits. Learn about depreciation, cost segregation, and the powerful short-term rental tax loophole that could save you big—even if you're not a full-time investor.
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15:34
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15:34
Abundance Mindset for Real Estate Success
In this episode, Tim Harstead reveals how an abundance mindset can transform your real estate journey. Learn how viewing money as a tool, embracing opportunities, and breaking free from scarcity thinking can help you achieve financial freedom and amplify your impact.
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10:55
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10:55
From House Hacking to Private Lending: With Bryce Matheson
The Landlording Show - Episode 18 - From House Hacking to Private Lending: With Bryce Matheson
In this episode, host Tim Harstead sits down with Bryce Matheson from Holbrook Capital to discuss Bryce’s journey from house hacking to managing millions in real estate investments. They dive into essential strategies for new and experienced investors, highlighting the value of long-term planning, creative financing, and transitioning to lending for passive income.
Key Takeaways:
The Evolution from House Hacking to High-Capital Lending: Bryce shares his journey, starting with his first rental property and eventually scaling to a multi-million-dollar portfolio.
Building a Sustainable Portfolio: Tips on financing multiple properties, handling property flips, and knowing when to expand or pivot.
The Pros and Cons of Self-Management vs. Property Management: Why Bryce self-managed dozens of units and what he learned along the way.
Passive Income through Lending: Discover why Bryce ultimately transitioned to real estate lending and how it allowed him to continue growing his wealth with less hassle.
Whether you’re investing in Chicago or elsewhere, this episode is packed with actionable insights for anyone looking to grow their real estate portfolio or diversify through lending.
The Housing Provider is the go-to podcast for landlords, property managers, and real estate investors who want to run smarter, more profitable rental businesses.
Every month, we break down the challenges and opportunities of providing housing, covering everything from tenant management and legal updates to maximizing ROI and avoiding costly mistakes.
Whether you’re a seasoned investor or a first-time landlord, we’ll help you navigate the business of housing with confidence.
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