Property Management Blog

By David Bovyn - Monday, October 12, 2026

Chicago Winter Prep: A Practical Checklist for Rental Property Owners

Chicago Winter Prep: A Practical Checklist for Rental Property Owners Chicago winter can put a building’s heating, plumbing, roof, and walkways to the test. A little preparation in the fall can help you catch problems early, respond faster when temperatures drop, and make y...

By Tim Harstead - Tuesday, September 29, 2026

August 2026 Market report for Lower west side (pilsen)

Pilsen has been a hot bed for Chicago Real estate investors since before covid and it shows now signs of slowing down. 2-4 unit buildings on the lower west side, otherwise known as Pilsen, have hit a new average high of 567K, up from 515K last August. Many inves...

By Tim Harstead - Friday, September 25, 2026

Chicago landlord secrets 9-24-26 CIty council postpones vote on pro and Nspire Hud guidelines

Chicago Landlord Secrets: Expert Insights on Property Management, Regulations, and Smart Investment DecisionsWhen it comes to Chicago property management, success requires understanding far more than just collecting rent. In a recent discussion between two seasoned Chicago landlo...

By Tim Harstead - Thursday, September 17, 2026

PRO Ordinance moves forward in Chicago housing committee

Chicago's Renter Protection Fight Heads to a Final Vote — But Not the One Landlords FearedChicago's yearlong battle over how far the city should go to protect tenants is about to reach a milestone. The City Council is set to cast its final vote on Mayor Brandon John...

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 David Bovyn - Friday, August 14, 2026

What Repairs Are Landlord vs Tenant Responsibility in CHA Housing?

One of the most searched and misunderstood topics in Chicago’s Housing Choice Voucher program is maintenance responsibility. Landlords often ask:Who pays for repairs?What is CHA landlord responsibility?What counts as tenant damage?What are Section 8 maintenance rules? Under...

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 ...