Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
The longer I do this, the more I am confident that an investor’s journey depends more and more on the resident they place in their unit over all other factors. Even paying 20% over the market gets fixed long term. Remember “Time Is Your Biggest Asset” as we say all the time on the Straight Up Chicago Investor Podcast.
Want Better Tenants? Do This First.
If you’ve ever had a tenant who paid rent on time, followed the lease, treated your property like it was their own, and even let you know when a leak started before it turned into damage, that person didn’t just make your job easier. They made you a better landlord.
Because here’s the truth: great tenants don’t just protect your asset. They push you to raise your standard of ownership. They give you time back. They create stability in your cash flow. They free up mental bandwidth so you can focus on growing your portfolio, not just surviving the next lease cycle. The right tenant doesn’t just fill a unit—they strengthen the entire operation.
Between the podcast and our management business I get to talk to dozens of Chicago and suburb landlords each week. It is crazy the extent investors will be flexible on rent just to keep a “Good Tenant” to renew! In just these past few months I have seen Chicago Landlords keep rent $400.00-$600.00 per month under what they could get in the market just to maintain this stability they are feeling as a Landlord.
I was on a call last week and I said, “you are losing $6,000 per year and if you had recent lease terms up he was down $19,000 per year in monthly rent against what I know he could be getting if he brought the rental rate up to where the other properties on the block are renting at. He told me “I am afraid I cannot find someone similar that will take care of my property the way this tenant does” so I offset my concern with that cost or that tax of receiving reduced rent.
I got off the phone and sort of chuckled because for every one “bad tenant” there are probably 3 amazing tenants like the one in my story above. What I have learned though is they don’t show up by accident. If you want better tenants, especially here in Chicago, it starts with how you show up as a landlord.
High-Quality Tenants Are Looking for High-Quality Landlords
We often hear landlords say, “There are no good tenants out there anymore.” But that’s not true. What’s more accurate is this: good tenants are bypassing rentals that look, feel, or operate like a liability. The good tenants are just as afraid to get a “bad landlord” and even though we as investors carry far more risk, a tenants fear comes with lower levels of satisfaction in life, safety concerns, and fears around their family’s overall comfort.
Think about it. The responsible, qualified renter with stable income, a clean record, and pride in where they live? They’ve got options. They’re not going to chase down an unresponsive owner. They’re not going to sign a lease filled with vague terms or take a gamble on whether maintenance gets done. They want a clean, safe, functional, well-managed space, and a landlord who respects them.
If your rental doesn’t communicate that up front—through the listing, the showing process, and your lease agreement—you’ll keep attracting the wrong crowd.
Start With Rent Pricing That Reflects the Market
One of the easiest ways to send the wrong signal to good tenants is by mispricing your rent. Too low, and you attract alot of people, giving you way too many options, and potentially missing out on the best one. Being too low obviously leaves money on the table and will overwhelm you with hours and hours of prescreening, more showings, and tons of applications you now have to responsibility underwrite and risk violating Fair Housing laws or the Cook County Just Housing Act.
Too high, this is where the real problems sit. When you set your rental price too high, especially in Chicago, you run into:
More vacant days
Risk of squatters
Less qualified applicants(this is where you get all the stories of why their application sucks)
Risk of settling for a less than ideal application
Attracting only tenants working with subsidies(not horrible but often the numbers don't work)
In Chicago’s market, pricing is hyper-local. Being even just $50 or $100 off can cost you weeks of extra vacancy.
Do you have a place on the market right now where you think the price might be off? Grab time with me or my colleague and we will give you a second option. (Schedule 15 minute call here)
Sometimes you are not sure what the market can allow you to rent your place out and that is fine. We rent out 30-40 Chicago properties per month and it isn't always clear what we can get for rent based on comparable rentals or maybe the property is super unique but we live by one rule which is adjust down quickly.
If you don't have 7-10 inquiries in the first 7 days you are too high
If you don't have 3-5 showings in the first 7 days you are too high
If you don't have 1 application in the first 10 days you are too high
Your Listing Is a Magnet—Make Sure It’s Attracting the Right People
Think of your rental listing like a dating profile for your property. If it’s sloppy, rushed, or full of stock phrases, it won’t attract the kind of people you actually want to live there.
Great tenants are looking for listings to attract them to your property. The key components that make a good rental listing are:
Solid Hookpoint - Every online listing has the opportunity for 20-40 words where you need to display the top 3-5 best things about your property. Might be location, neighborhood highlights, but most importantly property features. If your headline only has info about the neighborhood that tells me your unit has nothing great about it.
Quality Pictures & Floorplans - Spend the $150 and get professional pics if you are unable to take great pics with your Iphone. It is easy to get great pictures with your cell phones these days but if you are one of those people that can't do it then pay someone. Remember you can reuse these pictures for future rental marketing or when you go to sell so the $150 cost is paid now but spread across multiple uses.
All The Costs - Disclose and be up front with all costs including move in fees, deposits, utilities, application fees, and anything else that will come out of pocket.
Ease Of Doing Business - The entire world wants things easier, faster, and cheaper these days and that is no different here. Make sure it is easy to find out more info.
Want our team to give your Chicago or Chicago suburb rental listing a free review. Schedule time here and we will advise you on easy steps to make sure you have the best listing on the block.
The Screening Process Is Your First Act of Leadership
This is where most landlords go wrong. They get tired, desperate, or optimistic—and rush the screening. But great tenants want to be screened. They expect it. It tells them you care about your property, about fairness, and about having a stable rental community.
If you’re not verifying income, calling landlords, checking public records, looking at their bank accounts, scanning documents for changes made, doing the math on pay stubs, talking to references, scanning social media, verifying past rent payments, and pulling credit reports, you’re not screening, you’re hoping.
And here’s the kicker: your tenant screening doesn’t just protect your property. It sets the tone for the entire relationship. When tenants know you operate with structure, they’re more likely to respect lease terms, communicate proactively, and stay longer.
If this all seems like too much don't do it half assed talk to our team about Tenant Placement services where we can do all this and even show you how to do it so you can do it yourself next time. Schedule a call today!
Set the Standard—and Then Deliver On It
Good tenants are drawn to professionalism and repelled by chaos. If your move-in process is confusing, your lease is vague, or your repair response is inconsistent, don’t be surprised if your ideal tenant becomes someone else’s.
The best landlords in Chicago have systems. Digital applications, digital leases, electronic fund collection, 24/7 work order lines, tenant portals, defined timelines on repairs, quality vendors, and clear communication channels. They treat tenants with dignity. And they follow through on what they say.
That level of operation doesn’t just attract better tenants, it creates them. Because when people feel safe, respected, and clear on expectations, they rise to meet them.
Moving is stressful and we broke down the moving process from the tenantspoint of view with New York Times Best Seller Joey Coleman. (Watch Here)
Understand That Great Tenants Want to Stay—But Only If You Give Them a Reason
Retention is where the real money is. When you have a great tenant, keeping them another year is always more profitable than trying to chase a higher rent with a new one.
And yet, many landlords forget that good tenants need to feel appreciated. Remember the lease renewal process starts 12 months earlier when the new tenant is moving in.
Work on your lease renewals early and remember there are rules about this in Chicago and Cook County.
60 Day Notice - If a tenant has been their 1-3 years
120 Day Notice - If a tenant has been there more than 3 years
For Kane, Will, Dupage, Lake, Mchenry, and Kendall most likely your lease says 30 days but across the industry sooner the better is best practice but 30 days is the closest you should push it.
If you want to keep raising rent if you need to keep aligned with what the market is doing then a renewal incentive can go a long way. A thank-you message or upgrade that 12 year old fridge. That makes them happy and prevents an emergency WO at a bad time somewhere in the nexe 1-24 months.
And remember—great tenants are being courted by other landlords too. If your communication drops off after the lease is signed, don’t be shocked if they start browsing listings again 5-6 months into their lease term.
Their zillow, redfin, Zumper notifications are still going and they may ignore them at first but some other Landlord’s solid hookpoint in their marketing may catch their attention!
You Become a Better Landlord by Choosing Better Residents
This is the part that often gets skipped. Everyone talks about how to fix a bad tenant situation. But not enough people talk about how the right tenant changes everything.
When you lease to someone who pays on time, reports maintenance issues early, and treats your property like their own, you have margin. You have time to improve. You’re not constantly reacting. You’re actually managing.
And that’s when the real growth happens. That’s when you finally stop being chained to your property and start thinking like an owner.
So, Want Better Tenants? Start Here
Price it right. Don’t guess—run a Free Rent Analysis and get real data.
Do Marketing. Professional photos and honest descriptions attract responsible renters.
Screen Like Your Future Depends On It. Verify everything. The time you spend here pays off for years.
Don’t Take Shortcuts & Outsource If Needed - Use a company like GC Realty & Development for Tenant Placement if you don't have the time or desire to do this right.
Deliver professionalism. Your behavior sets the tone for theirs.
Appreciate good tenants. People stay where they feel respected and secure.
Current or future investors have such a great opportunity in this great metro we call Chicago but a lot of investors think the hard part is finding a deal to invest in but the real work, the money making activities is in the tenant placement and ongoing management. We tell Chicago investors all the time that you have to treat your rental operation like a business. No different than your coffee shop you love. The best landlords in this city don’t just find great tenants. They attract them by being the kind of landlord the best tenants want to rent from.
And that’s the kind of win that pays you back year after year.
Need Help Managing Your Chicago Property?
👉 Schedule a call with our team and learn how GC Realty & Development helps landlords win long-term
Or tune into the Straight Up Chicago Investor podcast and learn from the city’s best (and worst) investor stories. Because success is never a straight line. And we’re proof of that.
There is a lot of information contained here if you plan on investing in real estate locally. It may seem overwhelming for those wanting to invest in the Chicago market, but it is really just a team sport. Who is on your investing team? Do you even have a team? GC Realty & Development, LLC. has a dedicated team of professionals that are willing to share their decades of experience in all facets of real estate. We handle everything from Brokerage, Leasing and Property Management. Whether you hire us or not, we are happy to provide you with our resources and expertise.
What gets me up in the morning and keeps me going twelve hours a day is the ability to add value to local area investors, in Chicago and beyond! Those who connect with me often hear me say that our goal is to bring value to everyone we come in contact with. We hope that in return, they will one day hire us for our Tenant Placement,or Property Management Services, refer us to someone they know, or leave us a review about our services. We would clearly love all three, however, we are happy whenever we get the opportunity to help!
Reach out today!
Partner / Co Host of Straight Up Chicago Investor Podcast
