Working with the City: How We Ensure Compliance Without Losing Time

Red Mug Investments

If you’ve ever tried to pull permits, schedule inspections, or navigate zoning codes in Chicago, you know it’s not for the faint of heart. The process can be complicated, time-consuming, and frustrating — especially when you’re under pressure to keep a project on schedule.

At Red Mug Investments, we’ve learned how to work with the City of Chicago to keep our multi-unit rehabs moving efficiently while staying fully compliant. Here’s how we do it.

Why Compliance Matters (Even When It’s a Headache)

Cutting corners might seem tempting when you’re racing the clock, but in real estate investment, compliance is non-negotiable. It protects your project, your buyers or tenants, and your long-term returns.

Here’s what we stay on top of for every property:

• Permitting for everything from electrical and plumbing to structural and exterior work

• Zoning regulations (especially important with multi-units and ADUs)

• Building code updates (which can change more often than you’d think)

• Historic or landmark restrictions, when applicable

• Required inspections, including occupancy, fire safety, and final walk-throughs

  
  

Skipping or delaying any of these can halt your project mid-build — or worse, require costly redos.

How We Keep Things Moving

We don’t just react to the city process — we build our timelines and workflows around it. Here’s how we reduce delays while staying fully above-board:

1. Do the Research Before the Deal

Before we buy, we’re already reviewing zoning, building violations, and permit history. We don’t make assumptions about what’s allowed on a property — we verify.

2. Build Relationships with City Officials

We’ve learned who to talk to, how to ask the right questions, and how to follow up without being a pain. Respect and communication go a long way.

3. Hire the Right Architects and Expeditors

We’re licensed architects who understand the city process and produce clean, approvable plans. When needed, we partner with trusted permit expeditors to help fast-track the paperwork.

4. Get the Permits Before We Swing a Hammer

It’s tempting to “just start the demo,” but we know that’s how you get red-tagged. We pull permits early and factor wait time into the construction schedule so we don’t lose momentum.

5. Stay Organized and Transparent

Every project has a paper trail — from permits to inspections to code updates. Our internal systems keep everything in one place, so we’re never scrambling to find what we need when the inspector shows up.

6. Anticipate (and Plan for) Inspections

We build inspection timelines into our project plans. That way, we’re never sitting around waiting for a green light — we’re moving on to the next task with confidence.

Lessons Learned From the Field

Here’s the truth: city compliance isn’t always smooth. We’ve had permits take longer than expected. We’ve run into surprise requirements. We’ve had to pivot plans based on zoning feedback.

But we’ve also learned how to navigate all of that without blowing the schedule or the budget.

The secret? Don’t fight the process. Understand it, respect it, and build it into your business model.

Why It Matters for Investors

If you’re an investor partnering with Red Mug or buying one of our finished rehabs, you’re benefiting from a team that’s done the hard part. We don’t cut corners, and we don’t deliver properties with compliance issues waiting to surface after closing.

Our goal is to create smart, well-built, legally sound properties that generate returns and peace of mind.

Have a deal in mind or want to partner on a future project? Let’s talk. We’re always looking to work with others who believe in doing it right the first time without losing time, momentum, or sleep.