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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
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If you’re a Chicago landlord, investor, or Chicago property manager, you’ve probably heard the same recycled takes a thousand times, rates are going to do this, the market is going to do that, wait for “blood in the streets,” then buy. In this Tuesday Tip, Mark Ainley cuts through the noise with a street by street, suburb by suburb view of what actually matters in Chicagoland for 2026, tight inventory, slow supply growth, and the one line item that can blow up your spreadsheet faster than any interest rate swing, Cook County property taxes.
Quick summary of Mark’s 2026 outlook, Chicago and suburbs
Inventory is still tight, and that’s not a short term problem. Mark’s point is simple, when there are only a few dozen homes for sale in an entire suburb, values and rents don’t exactly collapse, they grind upward. Meanwhile, Chicago’s supply pipeline is still nowhere near “catching up,” especially compared to Sun Belt markets that have been building like crazy.
Questions we answer in this episode
Q: If I’m thinking about buying in 2026, what’s your answer
Mark’s answer is blunt, yes, buy it, assuming the deal works. His reasoning is that inventory is still tight across Chicagoland, and that doesn’t create a market where you get endless second chances. The bigger risk for a lot of people is waiting, consuming content, and never pulling the trigger.
Q: What should I actually account for in my underwriting
Mark flags one big one for Cook County, property taxes, especially with reassessments in certain townships. He talks about budgeting for meaningful increases so you’re not shocked later. Beyond that, his focus is practical, understand the suburb or neighborhood you’re buying in, any rental licensing requirements, and the maintenance reality of the building, because that’s what hits your cash flow month after month.
Q: Do interest rates change your mindset
Not much. Mark’s point is that today’s rates are still historically low compared to what previous generations dealt with, and the ultra low 2.5 to 3 percent era was the anomaly. He also makes a great landlord point, your rate is usually fixed and predictable, your taxes are not, and predictability matters when you’re planning for long term ownership.
Q: What do you think about the constant “blood in the streets” predictions
Tom basically says he’s heard it nonstop since rates moved in 2022 and 2023, and in Chicago it’s been slow and steady, not dramatic. Mark’s underlying message is that a lot of the loudest predictions are built for thumbnails, not for owners who actually operate in a specific Chicago neighborhood.
Q: Why do some Sun Belt markets feel different right now
Because they built a lot more. Mark points out that some metros issued huge numbers of new construction permits year after year, and that kind of supply can change the rent story. Chicago hasn’t had that same volume, so the supply side pressure that can cool rents elsewhere is just not the same here.
Q: What should I do if I don’t even have a niche yet
Do something. Mark’s advice is that the gap between “I’m interested” and “I took action” is what decides whether 2026 is a breakthrough year or another year of planning. Start with a handful of moves, learn, tighten the model, then keep going.
Show notes and timestamps
- 00:00 Intro, why 2026 feels more “certain” locally than the headlines suggest
- 00:42 Ignoring dramatic internet predictions, focusing on street by street reality
- 01:21 Should I buy in 2026, Mark says yes, inventory is still tight
- 02:00 Underwriting realities, Cook County taxes, licensing, maintenance
- 02:53 Interest rates in context, the 2.5 to 3 percent era was the anomaly
- 03:41 Mark’s 2026 focus, buy more, keep working the niche, keep plowing forward
- 04:48 Blood in the streets talk vs Chicago slow and steady reality
- 05:18 Why Sun Belt supply is different, Chicago’s construction pace has been flatter
- 06:12 Apartment permit slowdown, what it means for city competition
- 06:58 Final message, know your numbers, stop waiting, take action
- 07:24 Chicago Fact, DePaul Blue Demon mascot trivia
- 08:07 Answer reveal, Dibs, and the sponsor shoutout
Takeaways for Chicago property managers and landlords
- Stop outsourcing your confidence to national headlines, Chicago is micro market driven, and your best edge is local knowledge.
- Underwrite taxes like they can move against you, because they can, and they are often less predictable than your mortgage.
- Tight inventory supports values and rents over time, especially when your region is not overbuilding.
- If you’re a city landlord competing with new construction, watch the permit pipeline, fewer new deliveries nearby can change your leasing season.
- If you don’t have a niche yet, action beats theory, do a handful of “somethings,” then refine.
Guest info
Guest Name: Mark Ainley, Founder and Partner, GC Realty and Co Host, Straight Up Chicago Investor Podcast
Guest Company Website: 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
