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Being a landlord in a big city can be an especially daunting job, but it doesn’t have to be. With the right strategies and diligence, managing your tenants can be a breeze. In this article, I’ll answer some of the most frequently asked questions I get as a licensed realtor, ultimately helping you streamline your landlord duties, improve tenant satisfaction and retention, and create a positive experience for everyone involved. Let’s get started exploring some effective ways to make your life as a landlord easier in the Windy City.


As a landlord, 95% of your happiness comes from the approach you take to communication with your tenants. Clarity is key. Start by giving tenants a comprehensive list of contact options, including your preferred method of communication, whether it’s phone, email, or text. To avoid issues, be very clear about the appropriate use of each communication method. For instance, I often encourage tenants to call me for urgent matters, send an email for non-urgent inquiries, and text for quick updates and simple questions.


A good strategy I’ve found is creating an email address based on the property address (like This works great as long as you’re monitoring that email: tenants feel heard and you’re not constantly being bothered by notifications. Gmail also has an option to auto-reply that you’ll look into it and get back within 24-48 hours.

If the issue isn’t important, or if it’s not a time-sensitive issue, tell them you’ll look into it and get back to them. Later, you can tell them that you’ll keep an eye on it, but it’s not a pressing issue.


If you’re not inclined to use email, you can give them your phone number and tell them to text. Again, try to communicate that you’ll get back within 24-48 hours. I strongly recommend that you tell them that phone calls are for emergencies only. For me, an emergency is one of two things:

  1. Water leak: A leak in the ceiling or under the sink is an immediate, time-sensitive concern that needs to be dealt with. Tell them to call a plumber if you don’t get back right away.

  2. Fire or police emergencies: Have them call 911 and then call you.

Alternatively, if you use an app to collect rent, then using that app for communication generally works great. However, if they’re not using it to pay rent, they probably won’t use it to communicate with you.

Ultimately, it’s important to respond to things with the right timing. Real issues deserve timely responses. For things you can’t fix or don’t think are worth the money—for example, a tenant may complain about a hallway needing new paint—you don’t need act as urgently.


Yes, landlords can require tenants to have renters insurance in Chicago. Doing so is actually usually beneficial for both the landlord and the tenant. It protects the tenant’s belongings in case of a problem like theft or a fire, and it provides liability coverage for the landlord in case the tenant causes damage to the property. This means that if a tenant accidentally starts a kitchen fire, the insurance will cover the cost of repairs, rather than the landlord having to pay for fixing it.

It’s generally a good idea to include a clause about renters insurance in your lease agreement. While you can’t require a specific insurance provider or agent, you can suggest reputable insurance providers and encourage them to get multiple quotes to ensure everything is properly covered.


A lot of landlords get anxious about tenants not paying rent or refusing to move out when their leases end, but don’t panic—it’s actually not a big issue. Most tenants are responsible and pay their rent on time, and in Chicago, you have legal protections to handle any issues that may arise.

Personally, I’ve only had two tenants in my life that I had problems collecting rent from. Both were during Covid, and both had warning signs in the credit check that I chose to ignore. Even in this worst-case scenario, it was relatively easy to deal with, and I got them to leave. Most people don’t want to create problems.

To further reduce the risk of this happening, have them sign a lease that clearly outlines the terms of rent payment and move-out procedures since this can decrease the risk of disputes and misunderstandings even more. I recommend keeping lines of communication open with your tenants throughout the lease term as well, as this can help catch any issues before they escalate.

I understand having worries about troublesome tenants, but there are so many ways to mitigate those concerns and handle the situation if any issues do arise. Remember to stay positive and proactive in your tenant management, and you’ll almost certainly find that things go smoothly the majority of the time.


1. Rental application: Ask potential tenants to fill out an application that includes employment information, rental history, and personal references.

2. Credit check: Reviewing potential tenants’ credit reports can give insight into their financial history, which can be a key indicator for their ability to pay rent on time.

3. Verify everything: Make sure to actually contact the tenant’s employer to confirm their employment status and income. It’s important to know that they earn enough to comfortably afford the rent.

4. Rental history: It’s also important to check any potential tenants’ rental history with their previous landlords to catch any issues they may have had with paying rent on time or with property upkeep.

5. Meet them where they live: There’s no reason you can’t meet the tenant in their current home. If the kitchen and bathrooms are relatively clean, that’s likely how they’ll keep your unit. Remember that they’ve likely cleaned up for you, so be careful if it’s in a bad state or looks distressed.


Maintaining the property is one of the most important responsibilities of being a landlord. Doing so effectively can help build trust between you and your tenants, and it ensures the property will stay in good condition.

Being proactive is the best way to stay on top of maintenance requests and repairs. Be sure to regularly inspect the property to identify potential issues before they turn into serious problems. You can also start a system of reporting and tracking maintenance requests to you can prioritize and schedule repairs effectively without losing too much time.

Something I’ve found great success in is building a network of reliable contractors and service providers, such as plumbers, electricians, and HVAC technicians. You can always reach out to to me if you need a reference. Building good relationships with these professionals can help you get quality work done on your timeframe and in your budget. As long as you listen to your tenants and stay on top of everything, your experience as a landlord will be great.


In my opinion, repainting every single time a tenant moves out is costly and time-consuming. I suggest only repainting if the walls are heavily marked or damaged. A good rule of thumb is to repaint every two to three tenants, or every few years, to keep the property looking fresh and appealing.

Another strategy is to simply touch up scuff marks and stains, only repainting the walls that need it. This often saves time and money while still keeping the property in great condition.

Ultimately, repainting depends on the walls’ condition, as well as your personal preference. If you choose to repaint, consider using a neutral color that appeals to a wide range of tenants and complements the property’s style. In the long run, a well-maintained property can attract higher-quality tenants and lead to fewer turnovers.


As a landlord in Chicago, you need to understand the laws and regulations about security deposits and move-out inspections. While collecting a security deposit from your tenants may sound like a smart idea, it’s not always advisable in Chicago. Due to the real estate laws in the city, landlords are required to hold security deposits in a separate, interest-bearing account, and the amount they can actually charge is very limited.

Personally, I recommend against collecting security deposits altogether. More often than not, they lead to disputes between landlords and tenants, and they can make move-out inspections more complicated. Instead of collecting a security deposit, I suggest you consider charging a move-in fee or using other strategies that ensure the property is well-cared for, like renters insurance.

Going back to move-out inspections, as a Chicago landlord, you’re legally obligated to give tenants a reasonable opportunity to be present during the inspection. You also must provide them with a detailed list of damages and deductions that will come from the security deposit or move-in fee. Don’t forget these requirements to make sure your move-out inspections are fair and transparent.

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