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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
If you’ve been waiting for Chicago to “cool off” so you can finally buy, I’ve got bad news.
The market hasn’t cooled. It’s gotten weirder, tighter, and more competitive in the exact ways that frustrate buyers and reward owners who already have real estate.
In this episode, we bring back Jason Wagner from Greystone Realty to break down what’s actually happening right now, not the hot takes, not the doom headlines, the real stats. We talk about why inventory is historically low, why buyers haven’t disappeared even with higher rates, and why the “prices are going to come down” crowd keeps getting proven wrong in Chicago.
We also get into what this means for investors: how to price flips, why turnkey can still be value-add, where the strongest appreciation and rent growth is happening, and why time is still the biggest weapon in this market.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Flood disclosure. If your lease involves any tenant access to a basement, garden unit, or even basement storage (yes, even if the unit is on the 40th floor), Illinois requires a flood disclosure. If you’re renewing a long-term resident and the disclosure is new, you can add it as a disclosure, but the broader point is lease requirements change and you need to stay current. GC’s approach is simple: new lease every renewal, even if it’s long.
Q: How hot is the Chicago market actually right now?
A: Chicago is seeing some of the strongest price appreciation in the country and it comes down to one thing: low inventory. Jason frames it through months of supply. Citywide inventory is around 3.1 months, which sits in strong seller-market territory.
Q: What’s a “normal” inventory level and why does that matter?
A: 3 months and below is a strong seller market. 4–5 months is more neutral. 5–7+ months starts leaning buyers’ market. Chicago has been stuck in low inventory mode since COVID, and it hasn’t normalized.
Q: Why are prices rising even with higher interest rates?
A: Because buyers didn’t disappear. Demand declined from the COVID frenzy, but has stayed relatively steady for the last few years. The real drop happened on the supply side: fewer sellers are listing, partly because of the lock-in effect (low rates, paid-off homes, fear of buying back into a competitive market).
Q: Why do some people say they’re seeing “cracks” in the market?
A: In a lot of cases, it’s pricing, not demand. Jason’s point is blunt: if you’re priced outside the range buyers expect, the property sits. Sellers confuse “overpriced” with “market slowing.”
Q: How should investors think about pricing a flip right now?
A: Use $25,000 pricing buckets (especially under $1M). Identify fair market value, then place the list price strategically in the right bucket. Stretching a little can work in spring, but stretching too far can kill momentum.
Q: Are buyers really still willing to take on work?
A: Yes, and it’s happening more than people realize. End buyers are buying properties that need updates because inventory is so thin, especially in school-district-driven areas. They’ll do the kitchen later, bathroom next year, but they want to get in the neighborhood now.
Q: Why is Chicago appreciating so strongly compared to other markets?
A: Chicago is a major metro that’s still relatively affordable, but it’s also supply-constrained. The conversation hits on the reality: Chicago didn’t experience the same explosive boom some cities did, and it also doesn’t build enough new inventory. That supply-demand mismatch keeps pressure upward.
Q: How do property taxes fit into this story?
A: Taxes are the “crack” that can hurt owners. If market values rise, taxes tend to rise, especially around reassessment cycles. Jason talks about running a 5-year model and baking in a year-three reassessment assumption. The point: don’t underwrite a deal using today’s taxes as if they’re permanent.
Q: Where is Jason seeing opportunity in Chicago right now?
A: Humboldt Park (especially the east side) came up as a strong area with real rent execution. He also likes Hermosa and still points investors toward the Northwest Side corridors like Belmont Cragin, Jefferson Park, and Portage Park.
Q: What does success look like for investors buying today?
A: The buyers who win are the ones who adapt: put more money down when needed, build partnerships, and run a real plan. He gives examples ranging from house hacking to 1031 buyers putting 40% down to make DSCR numbers work.
Q: What’s Jason’s outlook for Chicago?
A: He’s bullish. His core thesis is simple: if inventory stays low and demand stays steady, prices keep trending up. His advice is to stop waiting for a dip that isn’t showing up in the fundamentals.
Show Notes
00:55 “Buy properties, sit on it, you’ll be good” and why the market is never normal
01:00 Housing provider tip: Illinois flood disclosure and what to do on renewals
02:22 Jason Wagner returns and the “bring sourdough next time” recap
03:19 Spring market reality: hot vs “cracks” depending on who you talk to
04:09 Months of supply explained and why Chicago inventory is historically low
05:42 Why sellers aren’t listing and the lock-in effect
06:12 Multiple offers are still common and pricing discipline matters
08:09 $25K pricing buckets and how sellers talk themselves into overpricing
09:18 Buyers taking on renovations because inventory is thin
10:34 Example: Oak Park inventory shock and how little is listed
12:11 Chicago affordability vs coastal perception and why outsiders think it’s a steal
14:22 Why “prices will come down” doesn’t match the current fundamentals
19:05 Property taxes: reassessment pain and how to underwrite it
22:21 Neighborhood pockets Jason likes: Humboldt Park, Hermosa, Northwest Side
44:17 Wagner Report stats: price appreciation and rent growth by neighborhood
Takeaways for Chicago Property Managers and Landlords
If your lease involves tenant access to a basement or basement storage, flood disclosures aren’t optional.
Chicago’s price growth is being driven by low supply, not hype.
If a property “isn’t moving,” check pricing before blaming the market.
Buyers are settling into renovations because inventory is thin, which keeps demand alive even at higher rates.
The biggest underwriting mistake investors make right now is pretending taxes won’t reset. Model the reassessment.
If you buy and hold through the messy first year or two, time starts doing the heavy lifting.
Guest Information
Guest Name: Jason Wagner
Guest Company: Greystone Realty
Guest Link: https://greystonerealtychicago.com/
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
