Second City Developers, LLC

04/22/2026

Behind every successful deal lies a meticulous evaluation process that transforms potential into profit.

Here’s my quick process:

1. Start with violations
Before I look at anything else.
Building violations tell you:

– how much work you’re really signing up for
– how long the city might drag you through it

Think of it as the property introducing its problems upfront.

2. Check zoning
This tells me the real upside.
What’s the max best use here?

Often, sellers may not fully understand the details of what they're offering, so it's essential to verify the information. When you request a zoning certificate from the city, they won't point out if you're actually zoned for more units than what was initially specified.

3. Run comps (all of them)

– As-is value
– ARV (sale)
– ARV (rental = your insurance policy)

If the deal only works one way, it’s not a deal—it’s a gamble.

4. Next, I review the photos and determine the rehab costs.

Yes, the pictures matter… but let’s not pretend they’re honest.

This is where experience (and a little skepticism) kicks in.

5. Tighten the comps and look for the “gotchas”

A few favorites:

– House pushed to the back of the lot? → knock ~40% off ARV
– Busy street? → buyers will remind you
– Funky layout? → so will your resale timeline

Evaluating deals isn’t about finding perfection.

It’s about spotting the problems faster than everyone else—and making sure they’re priced in…

Because they always show up

04/20/2026

Sight-unseen offers as an operator aren’t crazy.

…but they do assume you enjoy a little chaos in your life.

A few realities no one puts in the listing:

• Your construction team = your survival plan
Because “surprise issues” are not if… they’re when.
And if your GC treats every problem like a winning lottery ticket, congrats—you’re funding it.

• Know your cost per sq ft like you know your coffee order.
If you need to “walk it to see”… you’re already behind.

• Contingency isn’t optional

That clean, bright listing could be hiding:
– water intrusion
– sketchy electrical
– something structural that makes your engineer sigh deeply

• Photos are… aspirational

They don’t show:
– mold
– moisture
– or that very specific, unforgettable cat p*e meets humidity smell

• Site stuff will humble you

Tight access, bad grading, weird layouts—
things that don’t show up in photos but absolutely show up in your budget.

Sight-unseen deals aren’t about being fearless.

They’re about being the person in the room who says:

“Yeah, this might be a disaster… but I already priced that in.”
And then somehow still sleeping at night.

Who’s still out here buying without seeing it first?

04/17/2026

10 years ago, I almost hired a contractor I “felt good about.”

Good personality.

Confident.

Talked a big game.

He asked for a $20,000 deposit.
Nothing unusual.

But something felt off.

So instead of moving forward, I went to one of his active job sites.

What I saw told me everything:

Disorganized
Slow progress
No real leadership on site

I walked away and later found out he left another project mid-job.

I see a lot of complaints lately:
• “Contractors are taking deposits and disappearing”
• “Why are they asking for 50% upfront?”

Here’s the reality:
The problem usually isn’t the deposit.
It’s what happens before you pay it.
Most people don’t know how to properly vet contractors, evaluate projects, or spot red flags early.
That’s where deals go sideways.

Today, I don’t move forward without:
• Visiting active job sites
• Calling references and asking specific questions
• Tying payments to actual progress
• Trusting my instincts when something feels off

And in many cases, I’m brought in to evaluate deals or step in when projects hit issues—whether that’s underwriting, construction ex*****on, or navigating city violations and stop work orders.

Real estate rewards discipline—and exposes shortcuts.

If you’re working on a project and want a second set of eyes before moving forward (or need help getting one back on track), feel free to reach out.

05/14/2025

Another successful flip in Lynwood. $299k list, multiple offers over ask.

09/26/2024

The Round Lake flip just hit the market 🤞🏾

12/17/2023

08/03/2023

Listing this Tuesday…

07/19/2023

Wrapping up in Libertyville!