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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

If you spend any time working in Chicago real estate, you eventually realize you’re playing a long game built around timing, neighborhoods, and understanding how the city evolves block by block. That’s why conversations like this one with Lawrence Dunning are so valuable. He’s an investor, developer-focused broker, and someone who has watched entire pockets of the city transform because of strategic new construction projects and long-term vision.

This episode breaks down how Chicago’s south and west side neighborhoods are shifting, why developers are targeting specific pockets, how new construction 3-flats are outperforming older rehabs, and what early investors need to understand if they want both appreciation and stability.

What Lawrence Dunning Shares in This Episode

Lawrence has a unique vantage point: he represents eight to ten developers who are actively shaping neighborhoods like West Pilsen, Washington Park, and the area surrounding Mount Sinai Hospital. Because he works closely with the people actually buying the land and building the product, he sees where the next wave of investment is going long before it hits the MLS.

Here’s what he breaks down:

Why new construction 3-flats are thriving in specific pockets
How developers strategically assemble lots to control comps
Why areas like West Pilsen and Washington Park still have major upside
How appraisals often lag behind reality in emerging neighborhoods
Why investors from California, Texas, Florida, and New York continue pouring money into Chicago
How zoning (RM4, RM5) creates massive advantages for developers
Why long-term time horizons are still the foundation of every strong portfolio
What risks investors must navigate, and why the payoff is worth it

This episode is packed with practical insights on how Chicago grows, how to evaluate emerging neighborhoods, and how investors can position themselves for the next 5–10 years.

Q&A With Lawrence Dunning

Q: What is the biggest advantage of investing in neighborhoods like Washington Park, West Pilsen, or Woodlawn?
A: The upside. These areas have massive amounts of vacant land, major public investment, and developers assembling dozens of lots. When a single developer commits to building 10–20 projects, they physically transform the block. If you're early, you get the best returns.

Q: What should investors understand about being “first in” to an emerging neighborhood?
A: Expect appraisal issues, lack of rental comps, and some pushback, from lenders, appraisers, and even other investors. You're betting on what the area will become, not what it is today. The headaches are the reason the upside exists.

Q: Why do new construction 3-flats often outperform gut rehabs on the South and West Sides?
A: Because existing stock has terrible layouts. The bedrooms are small, the floor plans are awkward, and the ceilings are low. New construction gives tenants large bedrooms, modern amenities, and efficient layouts. Vacancy is lower and rent speed is faster.

Q: What price range should developers look for when buying lots in Washington Park today?
A: Anything under $100,000 is solid. Some trade in the $50K–$70K range depending on frontage, depth, and zoning. RM4 or RM5 zoning is ideal because you can build 3–4 units without fighting for variances.

Q: What is the most common mistake new investors make?
A: Waiting for the perfect deal. Your options only appear once you own something. Rates drop? You refi. Inflation spikes? Rents go up. The people who wait are always the ones priced out later.

Q: What advice do you have for new agents trying to grow into the investor/developer niche?
A: Get a niche. Learn one area, one product type, or one investor strategy better than everyone else. Wealthy clients value people who save them time and can tell them exactly what’s happening on a micro level.

Q: Is Chicago still investable despite politics, taxes, and crime?
A: Yes, if you play the game correctly. Chicago pushes development money into the exact neighborhoods where investors are buying land. The South Side has tens of millions earmarked for redevelopment. You follow the money and you’ll win long term.

Q: How should investors think about long-term strategy?
A: The Midwest rewards patience. If you want quick money, go gamble on crypto. If you want real wealth, buy now, hold long term, and let appreciation + rent growth do the work. Time is your greatest asset.

SHOW NOTES

00:00 – Opening banter, accents, past episodes, and Mark hiring for a maintenance director.

01:07 – Discussion on managing South Side properties and why new construction matters in tougher areas.

02:56 – Housing Provider Tip of the Week: Vevor adjustable handrails for Section 8 and inspector requirements.

04:20 – Welcome back to guest Lawrence Dunning and the story of showing up in a gas station t-shirt after elbow surgery.

07:04 – Running a marathon in Antarctica, extreme training, and lessons from pushing physical limits.

10:15 – Lawrence’s 20-year journey in Chicago real estate and evolution into development-focused brokerage.

12:00 – How developers assemble lots, create comps, and force appreciation with long-term planning.

14:38 – Advice for new agents building a niche and attracting real investor clients.

16:23 – Why out-of-state investors trust Lawrence to guide them into Chicago multifamily markets.

20:02 – Becoming “the guy”, building systems, providing solutions, and earning referrals.

23:12 – How Chicago’s market changed since 2020 and what’s coming next.

26:11 – Challenges of pioneering neighborhoods: low appraisals, lack of comps, and skeptical lenders.

30:23 – Neighborhood analysis: West Pilsen, Mount Sinai corridor, and why Washington Park is heating up.

34:00 – Why Pilsen floor plans struggle, why tenants prefer new construction, and how deep lots shape layouts.

37:00 – Lot pricing, zoning advantages (RM4, RM5), and how zoning changes development returns.

40:01 – Lawrence’s personal development challenges, easements, legal delays, and real-life headaches.

42:36 – How time rescues bad deals and the story behind firing a building during COVID.

45:01 – Macro outlook on Chicago, political realities, and why capital continues flowing to the South and West Sides.

48:33 – Long-term appreciation, block-by-block transformation, and how developers reshape neighborhoods.

51:24 – Advice for first-time buyers and why waiting for perfect timing holds investors back.

53:12 – What Lawrence does for fun: jiu-jitsu, cold plunges, running, and daily discipline.

55:10 – Book recommendations and why vacations are the best time to actually read.

56:02 – Chicago fact: DuSable Museum location and the $50 gift card winner.

Key Takeaways for Chicago Landlords & Investors

Neighborhood transformation is predictable when you follow where developers acquire land.
New construction 3-flats outperform gut rehabs in rent, occupancy, and tenant demand.
Zoning matters. RM4 and RM5 lots open the door to better returns and larger layouts.
Emerging neighborhoods require patience, but payoffs are significantly higher.
Appraisals lag reality, especially in early-stage investment pockets.
Buy sooner than you feel ready. Time smooths out the bumps.
Relationships and knowledge are your strongest investment tools.

Guest Name: Lawrence Dunning
Guest Company: Fulton Grace Realty
Guest Link: https://www.linkedin.com/in/lawrence-dunning-mba-2b97a120

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,