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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
In this episode, Mark Ainley shares a live presentation from the WSBOA meetup, now part of the Neighborhood Building Owners Alliance. Instead of talking about property management, screening, leasing, or new landlord laws, Mark breaks down the investing he has personally done over the last 30 months.
He walks through 15 deals, including buy-and-hold ranch homes, quick flips, sale leasebacks, industrial real estate, cost segregation, private money, partnerships, and a few mistakes that cost real money.
For Chicago real estate investors, this episode is a reminder that opportunity still exists, but you need a network, fast decision-making, multiple exit strategies, and the willingness to keep taking action even when every deal still makes you nervous.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Water always finds a way. Before spending money on big repairs, check the simple things first, like gutters, downspouts, grading, and drainage. But if the problem is bigger, cheap Band-Aid fixes usually come back to haunt you.
Q: Why did Mark choose this topic for the WSBOA meetup?
A: Mark wanted to force himself to review the investing he has done over the last 30 months. He had been buying, selling, holding, and partnering on deals, but had not fully processed what worked, what failed, and what he learned.
Q: What kind of properties was Mark originally trying to buy?
A: His original target was simple: brick ranch homes in DuPage County, ideally in towns without rental licenses. He wanted properties with strong resale value, manageable rehabs, good rent potential, and long-term appreciation.
Q: What was Mark’s first deal after getting back into investing?
A: The first deal was a small Downers Grove property bought for $227,500. The house was small, but the lot had strong value, the rehab was manageable, and the property worked as a long-term rental.
Q: What mistake did Mark make on the Downers Grove deal?
A: He did the rehab without getting the water meter situation handled first. He also learned that even small design decisions matter, like putting way too many recessed lights in a small house.
Q: Why does Mark prefer avoiding rental licenses?
A: Rental licenses add another layer of inspections, permits, timing, and cost. Mark is not anti-permit, but he prefers fewer municipal hurdles when trying to operate clean, simple rental properties.
Q: What was Mark’s best residential deal?
A: One of the biggest wins was a sale leaseback in unincorporated Schaumburg. He bought the house from a longtime owner, let them stay as tenants, improved the kitchen, and ended up with strong equity after the refinance.
Q: What did Mark learn from his first syndication?
A: Mark learned that raising money is not as easy as just calling your network. Many people in his network were operators or active investors, not passive investors looking to place capital into someone else’s deal.
Q: Why did Mark end up doing more flips than expected?
A: His original plan was to buy and hold, but the market presented opportunities to flip. When owner-occupant demand is strong and the numbers make sense, sometimes the best move is to take the profit and move on.
Q: What is Mark’s biggest takeaway from doing 15 deals in 30 months?
A: Speed matters. The most successful investors go from decision to action faster. Mark calls it velocity of decision. Real estate investing is simple, but it is not easy, and hesitation can cost years of missed opportunities.
Show Notes
06:09 Housing provider tip: water penetration, gutters, drainage, and why Band-Aid repairs do not last
08:11 Mark introduces his investing background and why he got back into doing deals
10:01 Mark’s original buy box: DuPage County ranch homes with no rental license
11:55 Deal 1: Downers Grove BRRRR, water meter mistake, and too many recessed lights
15:02 Deal 2 and 3: Bartlett, Hoffman Estates, rental licenses, and Federal Pacific panels
20:09 Sale leaseback strategy in unincorporated Schaumburg and keeping the tenant in place
27:56 First industrial syndication in Mundelein and lessons from raising capital
30:36 Using a quick Downers Grove flip to help fund an Itasca buy-and-hold
36:50 Hanover Park win, Elgin miss, and the reality of ARV mistakes
46:25 Final takeaways: inventory, partnerships, funding, cost segregation, and velocity of decision
Takeaways for Chicago Property Managers and Landlords
There is still inventory in Chicagoland, but most of it comes through relationships and networking.
Know your buy box, but stay flexible when the market gives you a better exit strategy.
Rental licenses can add cost, time, and headaches, especially for smaller buy-and-hold investors.
Every deal should have more than one exit strategy.
Small rehabs can be riskier than full rehabs if one hidden issue destroys the budget.
Sale leasebacks can work when the seller wants liquidity but also wants to stay in the home.
Private money from friends and family can be useful when the relationship and expectations are clear.
Partnerships work best when each person brings something different: money, time, construction knowledge, or operational skill.
Cost segregation can be powerful for long-term holds, but it needs to match your tax situation and hold period.
The investors who win are usually the ones who make decisions and take action faster.
Guest info
Guest Name: Mark Ainley
Guest Company: GC Realty & Development LLC
Guest Link: www.gcrealtyinc.com
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,
Founder, Partner, Podcast Co-Host, and Investor
