Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
There’s a lot of talk about how veterans can transition into civilian life and build financial freedom, but few people are actually putting the pieces together like DuBois Toy. A Chicago native, Air Force veteran, cybersecurity pro, and real estate investor, DuBois combines military discipline with tech automation to create scalable systems for property investing. From AI-powered tenant screening to maximizing VA loan benefits and boosting rental income through room-by-room leasing, his approach is a blueprint for veterans and civilians alike looking to succeed in Chicago real estate investing.
In this episode of the Straight Up Chicago Investor Podcast, DuBois shares how his first multifamily purchase with a VA loan set him up for long-term wealth — and why only a fraction of eligible veterans are taking advantage of this life-changing benefit. He breaks down how Chicago property managers can leverage automation to save time, how rent-by-room strategies can double cash flow, and why Chicago’s market fundamentals keep him investing here.
Whether you’re a veteran wondering how to use your VA loan, a landlord looking for better screening systems, or an investor curious about maximizing income on your units, this episode offers practical, actionable steps to move forward.
Questions We Answer in This Episode
Q: How do you use AI in your property business?
A: I built AI bots to automate my tenant screening process and deal analysis. Applicants fill out a pre-screening form, and the AI flags red flags, verifies income, and organizes data so I can make better decisions. I also created a deal-finding bot that evaluates properties based on Chicago-specific parameters, saving me hours every week.
Q: What is the biggest advantage of the VA loan for veterans investing in Chicago?
A: Zero percent down and no PMI. In most counties, the VA loan entitlement is $800,000, backed 25% by the federal government. You can buy a multifamily property, live in one unit, and rent out the rest — sometimes even getting cash back at closing. It’s also assumable, and in Illinois, certain disabled veterans qualify for massive property tax reductions.
Q: How does renting by the room increase cash flow?
A: In many neighborhoods, a three-bedroom might rent for $1,500 as a whole unit. But renting each room individually for $700–$1,000 can push that total to $2,100–$3,000. It’s more management and turnover, but the income difference is huge — especially near colleges or hospitals.
Q: What’s a key lesson learned from tenant issues or evictions?
A: Always run a nationwide background and eviction check. Early in my investing, I relied on a partial check that didn’t include Illinois, and I inherited a tenant with an extensive eviction history. That cost me over $15,000 in lost rent and repairs.
Q: How can veterans work together to buy larger properties?
A: The VA loan allows multiple veterans to combine entitlements for bigger deals. Two veterans can buy up to a six-unit, three veterans can buy a seven-unit, and so on — as long as it’s owner-occupied. I’m currently teaming up with other vets to target small commercial properties in Chicago.
Q: What veteran resources are often overlooked?
A: Besides the VA loan, veterans have access to the GI Bill for free education or trade training, VA case workers for mortgage assistance, and significant property tax exemptions for service-connected disabilities.
Q: Why keep investing in Chicago?
A: Chicago’s appreciation rates, rental demand, and neighborhood growth make it a strong long-term market. Even with high leverage, the rents support the payments, and vacancy risk is low if you buy in the right areas.
Show Notes
00:00 – AI automation for tenant screening and deal analysis
04:40 – Helping homeless veterans with resources
06:47 – Automating data extraction from emails and spreadsheets
14:18 – Benefits of reducing tenant screening workload
16:20 – DuBois’ path from Air Force service to real estate
22:01 – First purchase: three-unit near Oak Park with a VA loan
23:57 – VA loan benefits and requirements
25:22 – Why most veterans don’t use their VA loan
26:46 – Eviction lessons and screening improvements
31:20 – Rent-by-room strategy for higher cash flow
36:44 – Educating veterans on VA loan advantages
38:39 – Combining VA loans for larger purchases
40:26 – Why leverage works in appreciating markets like Chicago
41:50 – Giving back and helping the veteran community
43:31 – Room-by-room rentals near UIC and Woodlawn
45:28 – Buying in winter to get better deals
46:32 – Building a team for automation consulting
48:05 – Property tax exemptions for Illinois veterans
50:53 – Why Chicago remains a strong investment choice
53:08 – GI Bill for education and trade training
56:07 – Competitive advantage: programming and API skills
56:59 – Advice for first-time buyers in Chicago
57:33 – What DuBois does for fun
58:14 – Recommended books and resources
59:17 – Importance of real estate meetups
60:46 – How listeners can provide value to DuBois
Takeaways for Chicago Property Managers and Landlords
- Automation saves time and reduces errors — AI can filter out unqualified applicants, analyze deals, and streamline data entry.
- VA loan for veterans is a powerful investment tool — zero down, no PMI, and large entitlements make multifamily house hacking possible.
- Room-by-room rentals can outperform traditional leases — especially near schools, hospitals, and transit.
- Nationwide screening is critical — avoid costly evictions by checking all states.
- Veteran resources go beyond loans — property tax exemptions, GI Bill training, and mortgage assistance programs can improve ROI.
- Chicago remains a strong long-term market — appreciation, rental demand, and diverse neighborhoods support sustained investing.
Guest Name: DuBois Toy
Company: Trading Technologies
LinkedIn: https://www.linkedin.com/in/dubois-toy-769434b7
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,
Mark Ainley
Founder, Partner, Podcast Co-Host, and Investor
