Property Management Blog

By Tim Harstead - Wednesday, September 9, 2026

Chicago Property Management Update: Storm Damage, the Heat Ordinance Deadline, and Where to Invest i...

Chicago Property Management Update: Storm Damage, the Heat Ordinance Deadline, and Where to Invest in the South SuburbsMark Ainley (GC Realty & Development) and I sit down every week to talk about what's actually happening in Chicago property management — not the th...

By Tim Harstead - Wednesday, September 9, 2026

Chicago Landlord secrets August 22nd

Chicago Property Management Update: The New Federal Housing Law, the FAIR Act, and Where We'd Actually Invest Right NowMark Ainley (GC Realty & Development) and I got into it again this week — a new federal housing law that just passed, the FAIR Act's answer to ...

By Tim Harstead - Monday, August 10, 2026

Fair and Accountable Illinois Rental, or FAIR, Ordinance

After the mayor released the full text of his Protect Renters' Rights ordinance, Alderman Gilbert Villegas (36th Ward) introduced a competing bill called the Fair Accountability in Rentals ordinance (FAIR). We do not have the full text yet as it is still being worked on, but ...

By Tim Harstead - Thursday, August 6, 2026

Chicago's Protect Renters Ordinance

Mayor Johnson has released the text for his new Protecting renters ordinance and as expected it is a bunch of new rules that will raise the rents on millions of Chicago tenants. I am going to break down how the law is currently written, please be aware that it is still in the ear...

By Tim Harstead - Wednesday, August 5, 2026

What Services Do Chicago Property Managers Provide?

If you own investment property in the Chicagoland area, you may have considered hiring a property manager but are unsure what property management services entail. Many investors think that they can just hire any leasing agent to help them manage their property, others think that ...

By Tim Harstead - Tuesday, August 4, 2026

Renting properties in Chicago's Morgan Park neighborhood

Morgan Park is often a forgotten part of Chicago's south side when it comes to real estate investors. It’s often overshadowed by the surrounding areas, like Beverly as a higher end neighborhood and West Pullman as a cheap option for renters who can not afford to move in...

By Tim Harstead - Thursday, July 2, 2026

5 Problems New Investors have with Property Managers

When you're just getting started in the real estate investing world, and you start a relationship with a new property manager, there are a few key areas that can make new investors question whether their new property management team is doing well or just out to make some mone...

By Tim Harstead - Thursday, June 25, 2026

Brandon Johnson's Rental Proposal

Mayor Johnson has lost his mind, and it's about to displace an entire community of renters. The Mayor has proposed sweeping rental laws that will cause housing for low to middle income homes to become even more scarce and much more expensive. Let's break down what we know...

By Tim Harstead - Monday, June 8, 2026

How to Switch Property Management Companies in Chicago without Losing Tenants

Change can be hard, no doubt about it, but it is often necessary. Your rental properties are often your retirement plan, if not your main source of income, and trusting it with your current property management company when they're not taking proper care of your building, tena...

By Tim Harstead - Wednesday, May 20, 2026

Investing in Chicago's Ashburn Neighborhood

Investing in Ashburn: A Deep Dive into the 60652 MarketWhile many investors focus on the North Side or the high-profile downtown markets, there is significant value, appreciation, and cash flow to be found on the South Side. Today, we are diving deep into zip code 60652, better k...