Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
We kicked off week five in a row of Chicago Landlord Secrets, and Tim set the tone right away. We’re still showing up, still talking shop, and still trying to help Chicago landlords and property managers stay ahead of what’s changing.
We started with AI, because whether you love it or hate it, it’s already in your day to day. I was thinking about it at the gym, because that’s the one time I’m not checking email or calling someone. It hit me how fast the last few years have moved, and how the 2020s are going to be remembered as a major turning point.
From there, we went deep into where AI is actually useful right now for landlords in Chicago, where it can get you in trouble, and how we’re handling things like renters insurance, self showings, and the scams that keep showing up.
AI is helping landlords catch fraud, but the scammers are using it too
Tim brought up something I completely agree with. AI can be better than the human eye at catching fake documents, especially paystubs and IDs. There are programs now that flag issues fast, and it’s getting harder for fraud to slip through when you have the right tools.
The problem is the other side is using AI too. A fake paystub used to look obviously fake. Now it can look clean, formatted, and believable. Tim explained it well: the best tools aren’t just “looking” at a document, they’re comparing it to patterns and databases. If a company normally uses a major payroll provider and your paystub looks homemade, that’s a red flag.
On our side, we use software for scanning, but there’s a catch. If someone submits documents after the application is already in, some systems won’t scan the late uploads. So when something feels off, I’ll run those documents through Claude. If you upload multiple paystubs, that’s usually where errors show up. Claude will check the math, catch inconsistencies, and even tell you when the template looks wrong compared to what a major company typically uses.
Prompting matters more than people think, and most people do it badly
I brought up Prompt Cowboy because I think a lot of people treat AI like magic, then get frustrated when the output is garbage.
Prompting is communication. If half the idea is in my head and only half comes out, I don’t get what I want. Prompt Cowboy helps you mind dump and turn it into something structured that AI can actually follow.
Tim said something that stuck with me. Prompt engineering might literally become a job people go to school for, because asking the right questions is the difference between getting value and getting junk.
AI can help you market rentals, but it can also create fair housing problems
We talked about the photo side too. AI can now do virtual staging and photo cleanup. You can take a vacant room and make it look furnished. You can swap a cloudy sky for a blue sky. You can even make a snowy driveway look presentable so your exterior photos don’t look neglected.
But the biggest warning I gave is on listing descriptions. A lot of landlords use AI to write rental ads, and that’s fine, but you have to tell it to avoid fair housing violations. We’ve seen descriptions generated that referenced things you just can’t put in a listing.
The other mistake people make is asking AI to write a description with almost no info, and then it just makes things up. If you give it the photos, the amenities, and the real details, it’s way better. The more you prompt it correctly, the less risk you take on.
Renters insurance is valuable, but I’m not forcing it right now
Tim asked if we require renters insurance.
This is one of those topics where we’re not perfectly aligned.
Right now, I don’t force it. The main reason is it’s hard to track. We used to require it, and we’d see people sign up, then cancel a week later. It turns into a constant chase, and it gets time consuming.
What we do instead is make residents initial the lease language that says if they don’t have renters insurance and something happens, we’re not covering their personal property. I use a simple example like groceries in a fridge. If the fridge dies and they just bought $400 in food, that’s not on the landlord. Renters insurance can cover it.
Tim’s side requires it as part of move in, along with utilities in the resident’s name and all funds paid. He also pointed out the liability piece is often what matters most to landlords, and that over decades of managing a large portfolio, actual claims where it “really mattered” are not as common as people assume.
Another big learning we discussed is hotel stays. If heat is out for a few days or a unit becomes temporarily unlivable, that hotel cost is often something renters insurance is supposed to cover. Tim shared a situation where they paid up front, the resident filed the claim, and then they had to chase reimbursement because the resident got paid and never turned it over.
My bottom line is renters insurance is great for residents, and it can help in those rare bigger moments, but the tracking burden is real, and landlords should understand what it does and does not cover.
Self showings can work, but you need rules, follow up, and signage
We got a question about self showing software in the North and Northwest Side, places like Hermosa and Logan Square.
Yes, we use self showings. We use it through Rent Engine now. We used ShowMojo previously. But we only use it on buildings where there’s no shared common area access. I’m not giving a key that opens a common hallway where other residents live.
The value is obvious. People want to tour when they want to tour. They want Saturday at 3. Your agent already showed at 10 and moved on. Self showings give flexibility, and that can lease units faster.
Even with self showings, I still want physical check ins. Our team stops by every couple days to make sure everything is good. Some owners use cameras, which reduces the need to run out there.
I also shared the disclosure language we use, because this matters. We’re not giving possession. We’re giving short term access. If someone stays longer than a set time, they’re trespassing. That’s a key part of protecting yourself.
Tim’s experience was similar, but he brought up something we ran into more on his side: winter issues where lockboxes freeze up, batteries die, and the system fails at the worst time. On our side, the bigger issue is the cheap lockboxes freezing. The best tip I gave is placement. Moisture creates the freeze problem, so keep lockboxes out of dripping areas, and avoid positions where water collects.
The real risk is scams, not just squatters
I shared a horror story from self showings. A woman got evicted, slept in her car, and used a self showing to move into a unit on a Sunday. That was brutal for the owner, and we covered a lot of costs. But when you step back as a company, it’s still a risk versus reward decision, because self showings can speed up leasing for everyone else.
Tim shared a scam example that’s even more common. A scammer duplicates your listing online, uses your self showing instructions, and tricks a real applicant into touring. The applicant is real, they check in with GPS, they follow the steps, then they text the scammer saying they love the place. The scammer says send money right now to take it off market. The victim sends money to someone who isn’t even in the country.
I had a story too where a scammer got a younger woman to pay them rent. We were lucky because we got her to file a police report with us, which clearly established she did not have a lease or the right to be there, and we got it resolved in one day without major cost.
The best protection tip Tim shared is simple and effective. Put notices inside the property and on the door. Multiple places. Tape them up. The notice should say if you didn’t come through the official channel or talk to the approved names and phone number, you’re being scammed, call this number. The scammer never sees those signs, but the applicant does, and it can stop the scam before money moves.
We went on a Chicago history detour, and I’m not mad about it
We got into how a lot of criminals would make great entrepreneurs if they chose a different path, and that led into books.
Tim brought up Freakonomics and how it dives into Chicago gang structure like a business. Then he recommended Gang Leader for a Day, which he said is an amazing book, and he’s listened to it twice.
I threw out another one I’m listening to right now, American Kingpin, about Silk Road, and the fact that it ties back to Chicago.
Then we went full Chicago history mode. I shared a wild one I learned: the reason we have expiration dates on milk in Illinois ties back to Capone forcing action after his niece got sick from spoiled milk.
We also talked about Capone properties, tunnels, and a Maywood building where the basement had tunnels, closed off areas, and rooms that were allegedly used as jail cells. Tim shared a story about managing property in Little Italy where garages had basements, and the history behind that.
Then I went even deeper and talked about tunnels from my grammar school to Ford City, tied to its history as a bomb manufacturing complex. Chicago has a lot of weird history, and a lot of it is still physically there, even if it’s sealed up.
We even did a Feng Shui quiz for Lunar New Year
It was Lunar New Year, and Tim had AI generate true or false Feng Shui questions, and he tested me on them.
I got a couple wrong, but the bigger point was that these beliefs are real for certain buyers and renters. I’ve absolutely had people walk into a property, immediately say no based on layout beliefs, and walk right back out. Whether you believe it or not, it can matter depending on the market.
My practical reminder for mid February is tax refunds can help collections
At the end, I brought it back to something useful.
It’s mid February. Tax refunds are coming. If you have residents behind or on payment plans, put that into the conversation. Build it into the plan.
I like getting a chunk payment from the refund to catch them up, and sometimes even get them ahead. Tim shared a strategy I like a lot. If someone always pays on the 7th or 8th, and they get a big refund, have them throw an extra month of rent on top. Now they can keep paying on their normal schedule, but they’re early instead of late. Your cash flow improves, delinquency drops, and they stop stacking late fees.
Questions I answer in this episode
Q: How can landlords use AI right now in a practical way?
A: I use it to catch fraud in documents when something feels off, to help review full applications, and to improve listing photos and descriptions as long as I’m careful about fair housing language and accuracy.
Q: What’s the biggest mistake landlords make when using AI for listing descriptions?
A: They give it almost no info, and it makes up details. The fix is to feed it real amenities, real facts, and even photos, and also instruct it to avoid fair housing violations.
Q: Do you require renters insurance?
A: Right now, I don’t force it because tracking is a pain and people cancel. Instead, I make residents initial lease language that we are not covering their personal property, and I encourage them to get coverage.
Q: Are self showings safe in Chicago?
A: They can be, especially for single family and units without shared common area access. You still need strong disclosures, check ins, and ideally cameras. Winter lockbox issues and scams are the biggest pain points.
Q: What’s the most common self showing scam you’re seeing?
A: A scammer duplicates the listing, uses the self showing process, then pressures the applicant to send money to take it off market. Posting official contact notices inside the property helps stop this.
Timestamped show notes
- 00:34 Week five of the live stream and why AI feels like a turning point era
- 02:50 AI use case for credit checks and catching fake paystubs and IDs
- 03:20 How I use Claude to scan paystubs, especially late uploads
- 05:05 Using AI to review full applications and dig for red flags
- 05:32 Prompt Cowboy and why prompting is like communicating in real life
- 06:10 Prompt engineering as a future skill and even a future job path
- 07:03 AI virtual staging and photo improvements for listings
- 08:50 AI listing descriptions and why fair housing language matters
- 10:31 Renters insurance debate and why I’m not forcing it right now
- 14:46 Hotel stays and how renters insurance can cover displacement costs
- 16:56 Self showing software in Hermosa and Logan Square and how we use it
- 18:46 Lockbox freezing, battery issues, and placement tips in winter
- 20:41 Horror story of someone trying to move in through a self showing
- 23:50 Scam story where a victim paid a scammer and how we resolved it fast
- 26:13 The most common scam pattern and how to protect applicants
- 27:00 Posting notices inside the unit to stop scams before money moves
- 27:52 Chicago gang business structure books and recommended reads
- 30:26 Capone stories, tunnels, and why Chicago history is weird and real
- 33:48 Lunar New Year Feng Shui true or false quiz
- 41:56 Tax refunds and how to use them to improve collections
Takeaways for Chicago landlords and property managers
- AI can help catch fraud in paystubs and IDs, but scammers are using AI too.
- If your software misses late uploads, I run documents through Claude to catch inconsistencies.
- Prompting matters, and tools like Prompt Cowboy help you get better output.
- AI can improve listing photos and virtual staging, but listing descriptions need fair housing guardrails.
- I don’t force renters insurance right now because tracking is hard, but I do require lease initials acknowledging we don’t cover personal property.
- Self showings work best when there’s no shared common area access and you still do check ins or use cameras.
- The biggest self showing risk is scams, so I like posting official contact notices inside the unit and on the door.
- Tax refund season is a real tool for collections, and getting residents one month ahead can change everything.
Guest Information
Mark Ainley
Founder & Partner – GC Realty & Development
Podcast Co-Host – Straight Up Chicago Investor
Tim Harstad
Founder – Chicago Style Management
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
