Chicago Property Management Blog

Let me be real with you from the start: I didn’t grow up thinking I was going to own a property management company. I wasn’t the kid dreaming of big buildings or flipping properties. I was the kid patching up his shoes to make 'em last another year, hustling side to side between divorced parents, and watching people around me struggle to get by. I didn’t grow up with much, but I grew up hungry.And that hunger taugh...

Let’s be honest: when most Chicago landlords hear "Section 8," they either lean in with interest or flinch with fear. And I get it.But what if I told you that Section 8 housing, when approached correctly or with property management professionals on your team, can provide stable income, long-term tenants, and even help improve communities.Section 8, officially called the Housing Choice Voucher Program, is federally funded...

MEET MIGUEL: A NEW LANDLORD WITH BIG DREAMS (AND NO GAME PLAN)Miguel had always wanted to invest in real estate. He did his research on Bigger Pockets and listened to local podcasts like Straight Up Chicago investor. He felt ready! So when he got a deal on a small two-flat in Chicago’s Belmont Cragin neighborhood, he jumped in.Miquel did his research on the front end about the neighborhoods pricing, average rents, proforma numbers...

If you’re a Chicago landlord who thinks tenant placement is just putting an ad on Zillow and picking the first person who has cash in hand — you’re setting yourself up for a costly mistake.Over the last 23 years we have made many mistakes in this department and we want to make sure others do not.  In cities like Phoenix or Columbus, maybe that works. But Chicago? We’ve got:The Just Housing Amendment - Change...

I have had the opportunity to own and manage properties in other larger and smaller cities across Chicago and the suburbs, it is just very unique when it comes to Property Management.  It isn't even just that cut and dry to say “Chicago”, because there is so much uniqueness within the 6 counties, 183 municipalities, and thousands of individual HOA’s that make up Chicago real estate.  If you’ve ever ...

Why Abandonment Isn't as Simple as It SoundsIn the world of property management, few topics generate as much confusion as abandonment. To a casual observer, it might seem straightforward: if a tenant stops paying rent and disappears, they must have abandoned the property, right?Not quite.In Illinois—and especially in Cook County and the City of Chicago—the legal definition of abandonment varies by location, and the wrong...

The Problem Chicago Landlords Face TodayPicture yourself showing up at your vacant Chicago rental to show a prospective tenant the place to lease. When you go to put your key in the lock at the front door for some reason it doesn't go in the slot or it goes in and doesn't turn?  You ask yourself “what in the … I was just here 2 days ago, I know this key works!”Then you walk around back, and you notice ga...

Chicago Landlord Secrets is a live show we record each week on my personal LinkedIn and the Straight Up Chicago Investor Facebook page.  Learn here what you need to know to grow faster & smarter in the Chicago real estate market. Join live and ask questions, or reach out anytime.  We help with Tenant Placement & Property Management, are here for Chicago investor questions as well. Connect Today!The rental landscape in ...

Chicago Landlord Secrets is a live show we record each week on my personal LinkedIn and the Straight Up Chicago Investor Facebook page. Learn here what you need to know to grow faster & smarter in Chicago real estate. Join live and ask questions or reach out after anytime. Connect Today!There is a lot to break down when it comes to rental licensing in Chicago and in the over 80  suburbs.  If you want to lease your property...

Chicago Landlord Secrets is a live show we record each week on my personal LinkedIn and the Straight Up Chicago Investor Facebook page. Learn here what you need to know to grow faster & smarter in Chicago real estate. Join live and ask questions or reach out after anytime. Connect Today! I get the opportunity to talk to hundreds of Chicago investors a year and the question often comes up “Should I Accept Pets”... or...