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This episode was different! In this live recording from the NSBC (Northwest Side Building Coalition) event, real estate powerhouses Joe Smazal and Ann Reilly join the Straight Up Chicago Investor Podcast to break down the latest leasing and sales trends in Chicago's apartment market. Whether you're a landlord, investor, broker, or property manager, this candid conversation sheds light on how properties are trading, what renters are prioritizing, and how policy shifts like the Housing Preservation Ordinance are affecting the game.
From zoning quirks to underwriting in an uncertain market, this episode covers it all—including a fun trivia segment that'll test your Chicago real estate knowledge!
Questions We Answer in This Show
Q: What are the biggest leasing trends shaping the Chicago market in 2025?
A: Joe and Ann talk about tenant preferences post-COVID, including a demand for updated finishes, private outdoor spaces, and flexibility in lease terms. Demand remains strong in well-located neighborhoods, especially for midsize units.
Q: How are apartment sales holding up in Chicago's current investment climate?
A: While rates have adjusted and financing is trickier, well-maintained properties in core neighborhoods are still moving. Buyer appetite remains strong for stabilized buildings with value-add upside.
Q: What is the Northwest Housing Preservation Ordinance and how does it affect investors?
A: The ordinance limits deconversions and demolition in certain areas, preserving affordable housing stock. Joe and Ann emphasize how this adds complexity to underwriting and neighborhood strategy.
Q: Are smaller operators still buying in Chicago, or is it all institutional capital now?
A: Chicago remains a fragmented market. There are still plenty of active local buyers, especially those targeting 2-12 unit buildings where institutions are less present.
Q: How are investors adapting to interest rate uncertainty?
A: Many are adjusting deal structures, locking in short-term rates, and emphasizing operational efficiency to improve cash flow while riding out market volatility.
Q: What compliance pitfalls are landlords overlooking right now?
A: The conversation hits on RLTO misunderstandings, early lease renewal violations, and fair housing mistakes—issues that can cause major headaches.
Q: How should landlords prepare for tenant renewals in 2024?
A: Be aware of the 90-day RLTO notice rule and don’t pressure tenants too early. Transparency and documentation are key.
Q: Are zoning and lot size still the main hurdles for small-scale development?
A: Yes. Joe explains how zoning categories like R-5 determine how many units you can build by right. Knowing the square footage and overlay maps are beneficial.
Q: What should Chicago landlords understand about community perception and tenant retention?
A: Reputation matters. A unit that looks neglected or has unresolved issues (like bullet holes from a past incident) can drive away quality renters. Respond quickly and present your property well.
Chicago Leasing & Sales Takeaways from the NSBC Event
Joe Smazal and Ann Reilly share real-time insights on how leasing traffic is behaving this year across neighborhoods like Logan Square, Portage Park, and Belmont Cragin. The panel dives into how rental pricing is reacting to inventory shifts and what sellers must understand when marketing their buildings.
With rising construction costs, more investors are turning to existing housing stock, pushing up demand in stabilized multifamily assets. Buyers still want cash flow, but they’re more sensitive to interest rates and building conditions.
Joe and Ann also discuss underwriting discipline—especially with changing taxes and local policies. Chicago's rental market isn’t for the faint of heart, but with the right information, landlords can navigate it effectively.
RLTO & Zoning Tips from the Trivia Segment
The episode wrapped up with a lively real estate trivia game. Some of the real takeaways include:
- RLTO Exemptions: Units occupied by employees and owner-occupied buildings with fewer than six units are exempt.
- Lease Renewals: Landlords cannot require tenants to sign new leases more than 90 days in advance. Violating this gives tenants the right to one month’s rent or actual damages, whichever is greater.
- Zoning Insight: In R-5 zoning (400 sq ft of lot area per unit), you can build up to 7 units on a standard 3,125 sq ft lot.
- Housing Preservation Map: Understand which addresses fall within preservation ordinances. This affects permitted unit counts and building modifications.
Show Notes
26:38 – RLTO exemption trivia and zoning challenges
27:43 – RLTO lease renewal notice rules and penalties
28:28 – Who is Daniel Ston and why does he matter?
29:32 – The history of Kletis restaurant and local Chicago legends
30:25 – RLTO lease renewal penalty details
31:58 – Longest running restaurant in Chicago trivia
33:17 – Belmont Cragin origins and first investment stories
34:05 – Northwest Housing Preservation Ordinance: what addresses are impacted?
34:43 – How many units can you build in R-5 zoning?
35:57 – How many firefighters are employed in Chicago?
36:35 – How much notice does a Portage Park tenant need before renewal?
37:17 – Name 5 “M” streets in Chicago: fun finale trivia
38:01 – Winner announced and thank-you from GC Realty
Guest Info
Guest Name: Joe Smazal & Ann Reilly
Guest Company: Interra Realty & Westward360
Guest Link: Joe Smazal & Ann Reilly
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,
Mark Ainley
Founder, Partner, Podcast Co-Host, and Investor
