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

If you spend enough time in Chicago real estate circles, you’ll hear the same conversations over and over again. Housing affordability. High barriers to entry. Zoning headaches. Neighborhood resistance. The assumption is that meaningful development only happens inside the city, and that everything outside the city limits is either sleepy, restrictive, or already built out.

This episode flips that assumption on its head.

In this conversation, we sit down with Jessica Erickson, an economic development leader reshaping how Woodstock approaches growth, density, and long-term sustainability. What’s happening in Woodstock right now is exactly what many Chicago suburbs talk about but struggle to execute: intentional density, walkable downtown living, investor-friendly leadership, and real alignment between public and private interests.

For investors, developers, and property managers watching affordability push farther from the city core, this episode offers a clear look at where opportunity is forming next, and how municipalities that “get it” are positioning themselves for the next decade of growth.

Why Suburban Economic Development Matters More Than Ever

One of the biggest takeaways from this episode is that suburban development isn’t about copying Chicago, it’s about doing what Chicago can’t always do efficiently.

Land costs are lower. Entitlement paths are shorter. Infrastructure is more adaptable. And when leadership is aligned, development doesn’t have to feel adversarial.

Jessica explains that construction costs are relatively consistent regardless of location. What changes is risk. In the suburbs, the right mix of demand, zoning flexibility, and political will can dramatically improve project feasibility.

Woodstock is a prime example. It sits on a Metra line, has an authentic downtown that’s been in place for over 150 years, and functions as a county seat with built-in employment demand. What it lacked, until recently, was residential density in the downtown core.

That’s now changing in a big way.

Downtown Woodstock’s Shift Toward Density

For years, Woodstock functioned primarily as a destination downtown, festivals, events, tourism, weekend foot traffic. What it didn’t have was residents living in the center of town.

That gap is now being addressed through a major market-rate multifamily initiative adjacent to the Metra station. The proposed development, currently in negotiations with Murphy Development Group, would bring close to 300 residential units into the downtown core.

This isn’t speculative density. It’s informed by real demand.

Woodstock already completed a four-story apartment building downtown, and it filled so quickly that waiting lists still exist today. That project served as proof of concept. The larger development is the natural next step.

For investors, this is what you want to see: incremental scaling backed by performance, not theory.

Navigating Community Resistance Without Killing Growth

Any time you mention density in a suburban setting, the same concern surfaces: “Not In My Backyard.”

Jessica doesn’t pretend that resistance doesn’t exist, but she makes it clear that it doesn’t run the decision-making process.

From a city leadership perspective, Woodstock’s comprehensive plan already calls for increased downtown density. Elected officials understand that residential concentration supports local businesses, stabilizes tax bases, and reduces long-term infrastructure strain.

Downtown business owners are overwhelmingly supportive. More residents mean consistent foot traffic, not just festival weekends. That consistency is what sustains restaurants, retail, and service businesses year-round.

The result is a city that listens, but still moves forward.

How Woodstock Uses TIF the Right Way

Tax Increment Financing gets misunderstood all the time, especially by smaller investors who only encounter it on large commercial deals.

Jessica breaks down how Woodstock is shifting its TIF strategy to be more precise and effective.

Instead of drawing massive TIF districts without shovel-ready projects, the city is now aligning TIF creation directly with specific developments. The Metra-adjacent multifamily project will receive its own dedicated TIF district, allowing increment to be generated almost immediately after completion.

This matters because timing matters.

A TIF district that doesn’t produce increment for a decade helps no one. A focused TIF that supports catalytic development creates reinvestment dollars early, which then fuel infrastructure, beautification, and additional projects.

For smaller-scale investors, the takeaway is simple: incentives are no longer optional in many suburban markets. Municipal participation has become a structural part of deal feasibility.

Route 47: Where the Next Wave of Redevelopment Is Coming

Outside the downtown core, Woodstock is also investing heavily in its Route 47 corridor, a major north-south artery connecting Route 14 to St. Charles Road.

The city is contributing roughly $16 million toward a $70+ million corridor project that includes infrastructure upgrades, utility relocation, landscaping, lighting, and streetscape improvements.

This isn’t cosmetic spending. It’s strategic repositioning.

Commercial corridors are cyclical. National chains move in, extract value, and leave behind outdated buildings. Woodstock’s approach is focused on adaptive reuse, ensuring that today’s developments can evolve into tomorrow’s uses without demolition and prolonged vacancy.

For investors with an eye on redevelopment, corridors like Route 47 represent long-term upside when municipalities commit to infrastructure first.

Opportunities for Small and Mid-Sized Developers

This episode isn’t just about seven-acre parcels and 300-unit projects.

Jessica makes it clear that Woodstock has significant opportunity for smaller developers as well, especially in the form of:

Downtown infill sites
Underutilized commercial buildings
One- to three-acre assemblages
Small multifamily and mixed-use concepts

Importantly, the city understands that a 12–24 month entitlement process kills small deals. That’s why Woodstock is actively updating its Unified Development Ordinance to reduce reliance on variances and special approvals.

The goal is predictability. When a city knows what it wants, the code should allow it by right.

What Makes Woodstock Different From Other Suburbs

Woodstock benefits from a leadership structure that mirrors the private sector more than traditional government.

Most elected officials have day jobs. The mayor comes from sales. Efficiency and accountability aren’t buzzwords, they’re expectations.

The city invests heavily in marketing, economic development, and technology. It views itself as a business entity competing for capital, not a gatekeeper rationing approvals.

That mindset shift is subtle, but it changes everything.

Questions We Answer in This Episode

Q: Why is downtown residential density so important for suburban cities?
A: Residents create consistent economic activity, stabilize local businesses, and support walkable downtown ecosystems beyond event-driven tourism.

Q: How does Woodstock decide when to use TIF?
A: TIF is applied strategically to shovel-ready projects that align with the city’s comprehensive and downtown plans, ensuring early increment generation.

Q: Are there opportunities for small developers in Woodstock?
A: Yes. Downtown infill, small multifamily projects, and adaptive reuse along Route 47 all present viable opportunities.

Q: How is Woodstock improving the permitting process?
A: By updating zoning and development ordinances to reduce the need for variances and allow desired uses by right.

Q: Why is Woodstock positioned differently than other far-out suburbs?
A: It has Metra access, an authentic downtown, county seat employment, and leadership aligned around growth and efficiency.

Key Takeaways for Chicago Investors and Property Managers

Suburban markets with aligned leadership offer real development upside
Density supports long-term downtown sustainability
TIF works best when paired with real projects, not speculation
Infrastructure investment attracts private capital
Smaller developers thrive where entitlement paths are predictable

Guest Information

Guest: Jessica Erickson

Company: City of Woodstock

Website: https://www.woodstockil.gov/directory.aspx?EID=18

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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.

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