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

When the market feels tight and opportunities seem scarce, some investors freeze — but others get creative. Jason Wagner, founder of Greystone Realty and author of The Wagner Report, is one of those who sees things differently.

Jason returns to the Underground to share how he’s helping Chicago investors find success by combining creativity, data, and execution. From assumable loans and innovative financing strategies to understanding the power of months-of-supply data, Jason explains how to thrive when everyone else is sitting on the sidelines.

In This Episode of the Straight Up Chicago Investor Podcast

Jason dives deep into the strategies that have helped him — and his clients — continue to buy in Chicago despite higher interest rates and limited inventory. He breaks down the mindset shift investors need to make: stop chasing cash-on-cash returns and start focusing on equity growth, tax advantages, and long-term appreciation.

The conversation covers everything from the Arlington Heights Bears stadium development and neighborhood data trends to assumable FHA and VA loans that allow buyers to take over low-rate mortgages.

This episode is packed with actionable insights for house hackers, agents, and investors who want to stay ahead of the curve.

Questions We Answer in This Episode

Q: Why does Jason believe Chicago is one of the best markets to invest in right now?
A: Because Chicago’s fundamentals are strong: low inventory, steady demand, and increasing prices. Unlike overheated markets in Florida or Texas, Chicago has balanced growth and remains one of the national leaders in year-over-year appreciation.

Q: What is the 2-1 or 3-2-1 buy-down strategy, and why does it matter?
A: It’s a temporary rate reduction program that lets buyers pay a lower interest rate for the first two or three years, using seller credits. It’s a way to “buy time” while rents stabilize or properties are improved — especially useful for house hackers renovating or turning units.

Q: What’s the biggest mistake new investors make in high-rate environments?
A: Waiting. Jason emphasizes that even “break-even” deals today can yield major equity and tax benefits tomorrow. The longer you wait, the more expensive the same property becomes due to rising prices.

Q: What makes Arlington Heights such a hot spot?
A: The incoming Chicago Bears stadium development. With 325 acres of land, a new Metra-accessible entertainment district, and national attention, Jason sees Arlington Heights as one of the most promising suburbs in the country for long-term growth.

Q: What are assumable loans and why are they a hidden gem?
A: FHA and VA loans can be transferred to new buyers at the original interest rate — sometimes as low as 2–3%. With lenders now offering second liens to bridge down payments, investors can secure blended rates in the 4% range, far below current market averages.

Q: How can data like “months of supply” help forecast Chicago’s market?
A: Months of supply measures how long it would take to sell all active listings if no new ones came on. Chicago’s current levels (under two months in most neighborhoods) show strong demand and continued upward price pressure — not a slowdown.

Q: What advice would Jason give to a 20-year-old investor starting out?
A: Get a W2 job, get pre-approved, and buy your first house hack. Live in it for a year, then repeat. After three to five years, you’ll own multiple properties with built-in equity and appreciation — all with low down payments.

Q: What inspired the Wagner Report, and how does it help investors?
A: Jason built it to give Chicago investors data-driven insight into neighborhood trends, appreciation, and inventory. The report helps agents and buyers make confident, analytical decisions — instead of reacting to national headlines.

Show Notes

00:00 – Kicking off with Jason Wagner and what’s new in his business
03:00 – The importance of handling utilities during tenant turnover
05:00 – The Chicago Bears’ Arlington Heights move and its market impact
08:00 – Why Arlington Heights may be one of the hottest suburbs in the U.S.
10:00 – Chicago’s Northwest Side investment performance: Portage Park, Belmont Cragin, Jefferson Park
11:00 – Explaining 2-1 and 3-2-1 buy-downs and how to use them
13:00 – How Jason partners with clients to co-invest in properties
16:00 – Low inventory and the importance of acting now
18:00 – Why Chicago prices keep rising while national headlines say otherwise
20:00 – How tax benefits and cost segregation amplify real estate returns
24:00 – Why cash flow isn’t everything — equity and depreciation matter
27:00 – The 100% ROI example of owner-occupant leverage
28:00 – Understanding FHA and VA loan assumptions
30:00 – How assumable loans create new opportunities for buyers
33:00 – Selling properties with assumptions — and skipping appraisals
35:00 – Why “2% debt is the asset” and how blended-rate loans work
36:00 – The story behind Greystone Realty and its investor-agent model
38:00 – How owning rental property changed Jason’s approach to clients
40:00 – Identifying riskier neighborhoods by months of supply
42:00 – The Wagner Report: using data to predict Chicago’s next moves
44:00 – The Midwest advantage — why our fundamentals are stronger
46:00 – Arlington Heights’ downtown, entertainment plans, and livability
48:00 – Jason’s passion for 75 Hard and personal growth
50:00 – Advice to 20-year-old investors: buy the first house hack now
51:00 – Book recommendation: The Five Levels of Wealth by Sahil Bloom
54:00 – Jason and Rachel’s Real Life Investing Podcast
55:00 – Final thoughts and resources for Chicago investors

Takeaways for Chicago Property Managers and Landlords

Chicago’s inventory remains extremely low, fueling price growth even with higher rates.
Act now — waiting for rates to drop could mean paying tens of thousands more for the same property.
Buy-down programs and assumable loans can make deals cash flow today.
Equity and tax advantages often outweigh initial cash flow concerns.
Arlington Heights is set to boom with the Bears’ move — positioning the northwest suburbs for major appreciation.
The Wagner Report is a must-follow for Chicago market data and investor trends.
Successful investing starts with one move: get in the game.

Guest Name: Jason Wagner
Guest Company: Greystone Realty
Guest Link: https://greystonerealtychicago.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,