Property Management Blog

By David Bovyn - Monday, September 28, 2026

Best Chicago Neighborhoods for Rental Investments

Best Chicago Neighborhoods for Rental InvestmentsBy Chicago Style ManagementWhere should you buy a rental property in Chicago?The answer depends on what you need that property to do. You might be looking for monthly cash flow, a building to improve over time, or a two-flat where ...

By David Bovyn - Saturday, September 26, 2026

Chicago Property Management vs. Self-Managing: What Does It Actually Cost You?

Chicago Property Management vs. Self-Managing: What Does It Actually Cost You?“Why would I pay a property manager when I can collect the rent myself?”It is a fair question. If you own a rental property in Chicago, keeping expenses under control matters. Management is ...

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 David Bovyn - Friday, September 25, 2026

Cost of Chicago property management

How Much Does Property Management Cost in Chicago in 2026?For most residential rental properties in Chicago, professional property management in 2026 typically costs approximately 8% to 12% of the monthly rent collected. Some companies use a flat monthly fee instead, and man...

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 - Tuesday, September 8, 2026

Property Management in Woodlawn

Property Management in Woodlawn, Chicago: A Housing Provider's Complete Guide (2026)If you own rental property in Woodlawn, you already know this neighborhood has changed dramatically over the past several years. With continued investment, strong rental demand, and ...

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 ...