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 for similar properties but he did not consider the Property Management side of the business that starts the day he closes.

He watched a few YouTube videos, downloaded a lease template online, and listed the unit on Facebook Marketplace. He grabbed an application from a friend back home in Boston.

First showing? A cash earning tenant who said all the right things. Miguel was excited because he felt he really connected with this potential tenant.

Since Miguel felt he could trust this guy he went against everything and did just a brief overview of his paystubs, credit report he brought, and did a quick Google search on his name. Then the same day Miquel handed over the keys after a handshake and a collecting just partial first months rent and half of the security deposit.

The new tenant told Miquel he would pay the balance of the security deposit one week later but Miquel couldn't get a hold of the tenant for 2 weeks and when he got a hold of him he had pushed him off to “tomorrow” for 5 days before just giving him $100 more dollars.

The first of the month rolled around and when Miquel reached out the tenant stopped returning calls and actually blocked Miquel's number.

Miquel went over to his rental to find 4 adults living there who he had no clue who any of them were. He reached out to GC Realty & Development right away and we helped him realize what he is up against and that he needs an attorney.

We referred Miquel to an attorney and seven months later, he was out over $11,000 in unpaid rent. The unit was trashed and they stole his appliances. Turns out, the “tenant” had a fake name, fake paystubs, and a history of doing this all across the west side of Chicago.

THE SCAM THAT WOKE MIGUEL UP

The tenant knew the rules better than Miguel did. They delayed every attempt to evict. Claimed housing discrimination and filed counter complaints. Miguel was spending his evenings online trying to figure out if there was a better way than having to go through a full eviction. Short of offering the tenant “Cash For Keys” there was nothing more he could do.

Eventually, he got the unit back. But not before losing time, rent, and confidence.

That’s when he called us.

TURNING THINGS AROUND: MIGUEL GETS STRATEGIC

Miguel realized something that changed everything:

“Being a landlord isn’t just about buying the property but it is about the years of managing that makes you the money. Managing starts with putting the right people in the units during leasing/screening”

Moving forward we helped him! We stepped in and gave him what every Chicago landlord needs which was professional advice and direction.

Miguel stopped managing on emotions and started managing on data.

WHAT MIGUEL LEARNED ABOUT CHICAGO LANDLORD TYPES

As Miguel grew his portfolio, he noticed something: not all landlords are built the same.

Some want full control. Some want to be hands-off. Some are in it for legacy wealth. Others are flipping within two years.

He started asking other investors how they operated. And that’s when he realized — success depends on knowing what kind of landlord you are.

THE BIG PICTURE: CHICAGO IS A DIFFERENT KIND OF MARKET

As Miguel dove deeper into the landlord game, he noticed how complex Chicago’s rental market really is. It's not just about rent prices and tenant relations — it's about:

City-specific ordinances like RLTO and RTLO
Ever-changing fair housing laws
Neighborhood-specific tenant expectations
Property conditions tied to inspections and compliance

In many cities, you can be a casual landlord. In Chicago? You need to be sharp.

WHICH CHICAGO LANDLORD ARE YOU?

We break this down in our blog: Chicago Property Management Solutions: Find the Best Fit for You

Whether you’re a full DIY landlord or ready to hand off the keys entirely, your strategy should match your personality, goals, and risk tolerance.

Miguel was done being reactive. He wanted steady growth, legal protection, and more time back — so he chose GC Realty’s full-service management.

NOW MIGUEL'S PORTFOLIO IS GROWING — AND STABLE

Today, Miguel owns three properties. He hasn’t had a late payment in over 3 years. He gets monthly reports, smart renewal advice, and peace of mind.

His biggest takeaway?

“I thought saving money meant doing everything myself. I learned that real savings comes from not making expensive mistakes.”

Whether you’re a first-time landlord or you’ve been at it for years, don’t wait for disaster to realize how high the stakes are.

HOW MUCH DO TENANT PLACEMENT SERVICES COST IN CHICAGO?

In Chicago and pretty much across Illinois hiring a firm like GC Realty & Development will cost a Landlord a fee equal to one month's rent.

What you get for that money is quality tenants, peace of mind, up to 60 hours of your year back, and lowered risk overall.

What is your time worth per hour? If it is worth more then $50.00 an hour then the math makes sense to buy back your time. If you are making over $100,000 per year then you are losing money trying to save money and rent the place yourself.

Time back, lower risk, and good tenant!

GET STARTED WITH GC REALTY TENANT PLACEMENT SERVICES

If you want:

Your time back
A legally compliant lease
A thoroughly vetted tenant
Zero phone calls from Craigslist scammers
Protection from modern rental fraud

Then let’s talk.

👉 Schedule a Call Today

👉 Learn About Our Leasing Process

👉 Get a Free Rental Analysis

Stop guessing. Start placing better tenants. Let GC Realty help you do it right the first time.

This is a lot of information you need to know if you plan to invest here in the Chicago market, and it may seem overwhelming but real estate investing in Chicago is a team sport. Who is on your real estate investing team? Do you have a team? GC Realty & Development has a team of resources and we are willing to share all of our 20+ years of experience in both real estate investing and Property Management in the Chicago market. We will do this whether you hire us or not.

What gets me up in the morning and keeps me going 12+ hours a day of work is the ability to add value to Chicago real estate investors. If we connect you will hear me say our goal of our company is to add value to everyone we come in contact with and in return we hope one day you will hire us for our Tenant Placement or Property Management Services, refer us to someone you know that needs Tenant Placement or Property Management Services, or will leave us a 5 Star Google review. We love to get all 3 from current and aspiring investors we get the opportunity to help!

Reach out today!