Ever wonder how some Chicago landlords go from one rental property to an entire portfolio of doors?
In this episode of The Housing Provider Show, Tim and Dave break down The Monopoly Strategy, a real-world approach to scaling your real estate investments without waiting for the “perfect deal.”

You’ll learn how to:
- - - Start small and build equity fast in the Chicago real estate market
- - - Use the 1031 exchange to grow your portfolio and avoid capital gains tax
- - - Understand what real cash flow looks like (and what most landlords get wrong)
- - - Handle risk, tenants, and the realities of property management in Illinois
- - - Hear real stories from Chicago housing providers who built wealth one door at a time

Whether you’re a first-time investor, experienced landlord, or just curious about property management in Chicago, this episode gives you proven, practical strategies for creating long-term real estate wealth.

🎙️ The Housing Provider Show is your guide to growing smarter as a landlord, covering investing, management, tenant tips, market updates, and landlord stories from the Chicago area and beyond.

🔗 Listen now and learn how to play real-life Monopoly

This episode of The Housing Provider Show is packed with strategies you can use right now.Host Tim Harstead (CEO, Chicago Style Management) sits down with Jackie Jablonski and Ivan Hernandez (Southwest Housing Provider Group, Chicago Friendly Landlord Group, Roofing by Hernandez) to break down:

- Why landlord communities in Chicago matter more than “how many doors you own”

- Real estate investing tips for buying 2–4 flats & multifamily properties

- Smart ways to raise rent, charge for extras, and boost cash flow

- Avoiding costly rehab mistakes + must-know landlord metrics

- Roofing insights every Chicago property owner should know (and how to avoid insurance scams!)

If you’re a Chicago landlord, housing provider, or real estate investor, this conversation will save you time, money, and stress.

Need property management in Chicago? Visit Chicago Style

Management https://www.roofingbyhernandez.com/

https://www.swhpg.com/

https://www.chicagostylemanagement.com/

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 portfolio

Whether 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!

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.

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.

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.

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 Cash Flow Myth: What Real Estate Gurus Don’t Tell You! In this eye-opening episode host Tim Harstead from Chicago Style Management, challenges one of the biggest myths in real estate investing — the promise of instant cash flow. While many gurus sell the dream of rental properties generating passive income from day one, Tim reveals the hidden truth about the real cost of property management. He dives deep into the importance of planning for maintenance, unexpected vacancies, and capital expenditures, all while highlighting the long-term value of real estate investment. Key Takeaways: The Myth of Cash Flow: Why it’s rare to see true cash flow in the first few years of property ownership. Building a Reserve Fund: The critical role of saving for property repairs and tenant turnover to avoid financial strain. Long-Term Gains: How real estate investors can start seeing substantial returns after five to ten years. Maintenance Planning: The importance of preventative maintenance and budgeting for future expenses like HVAC systems, roofing, and plumbing. Chicago-Specific Insights: Tips on handling tenant-friendly laws in Chicago and ensuring your rental properties are set up for long-term success. Whether you’re a new investor or a seasoned landlord, this episode offers a reality check that can help you build a sustainable real estate portfolio and avoid common pitfalls. . . . . . . . . . Why should you have a property manager? Reach out at www.chicagostylemanagement.com to find out. https://www.chicagostylemanagement.com/ CHICAGO STYLE MANAGEMENT 3341 S Lituanica Ave Chicago, IL 60608 224-601-5415

In this must-listen episode, host Tim Harstead sits down with Attorney and Realtor Tosh Chandy to break down the latest legal changes shaking up the real estate market. With new regulations set to take effect on August 17th, Tosh brings a unique perspective as both a legal expert and a practicing realtor.

Things that you should be doing to save yourself some money and things like that after you close in Chicago.

On this episode of the Landlording, we interview Laura Dantuma, a mortgage broker from Femme Capital, and discuss.How to use an FHA loan to buy investment propertiesCan you use FHA loans to buy more than one investment property?What are the different types of loans you can use to buy real estate investments?Why you should use a mortgage broker vs going through a bank?What do you need for a down payment when buying an investment propertyas well as answering many more questions about lending on your investment propertiesIf your looking a loan on your next property reach out to Laura at:laura@femmecapitalpartners.com630-939-9000855-44F-EMMEWhy should you have a property manager? Reach out at www.chicagostylemanagement.com to find out.

https://www.chicagostylemanagement.com/CHICAGO STYLE MANAGEMENT3341 S Lituanica AveChicago, IL 60608224-601-5415

Episode 13 - Optimize Your Lease

From smoking policies to pet regulations, and missed appointments to unauthorized occupants, we delve into crucial lease clauses that can protect your property and streamline your management process. Don't miss out, ensure smooth tenancies and maximize your rental income.

Strategic Estate Planning Guest: Security Benefits Center Dive deep into the world of estate planning with our latest podcast episode! Join Tim Fordham & Ben Smith from the Security Benefits Center as they explain the intricate details of trusts, tax implications, and the probate process. Gain practical tips on protecting your assets and ensuring your family's financial security. ** If you are looking to set up an estate plan or a trust please give Tim Fordham a call and mention you heard about him through Tim at Chicago Style Management, and receive $200 off of your fees! You can call Tim at 616-500-0120 or email him at timf@gosbc.net **

In this episode, host Tim Harstead explores how to expand your portfolio using the Monopoly strategy.

Today, we have a special episode featuring our host's $100 challenge. If you've ever thought about getting into real estate but felt held back by financial constraints, this episode is for you!

Join us as we break down the barriers to entry in real estate investing and show you how to overcome the hurdle of a down payment. Our host shares valuable insights and strategies that prove anyone can enter the world of real estate with determination and the right mindset.

On today's episode, I'm going to do a Q&A. We're going to go and take some questions that we got off of Facebook groups and answer them. Always check with your attorney before doing anything.

ENJOY!

We're going to give you some good tips today on how to best save money and things that you should be doing to make sure that you're going to be in a spot where your profits stay high.

Explore the strategies for building your portfolio, whether aiming for retirement tranquility or an empire of income. Join us on this insightful adventure!

#RealEstateInvesting #InvestmentGoals #SuccessInRealEstate #chicago

Join Tim Harstead & attorney Tosh Chandy in this podcast dedicated to unraveling the legal intricacies of the Chicago real estate scene. Discover essential strategies for success, whether you're dealing with building violations, LLC representation, or other legal challenges. Get the inside scoop on how to thrive in Chicago's dynamic real estate market.

In this episode, Tim from Chicago Style Mgmt delves into the critical mindset needed for successful property management, emphasizing the importance of planning for capex projects, building reserves, managing taxes, and understanding the real estate cycle. Subscribe now to gain valuable insights and secure your financial future through real estate investing.