Straight Up Chicago Investor Episode 393: Chicago Veterans’ Guide to Real Estate Success with DuBois Toy
Aug 14, 2025
DuBois Toy, a real estate investor and veteran, shares his journey from house hacking to mastering rental strategies. He emphasizes the benefits of VA loans and tax exemptions available for veterans, making real estate investment more accessible. DuBois also discusses leveraging AI to streamline property searches and tenant screening processes. His insights into maximize cash flow through room rentals and the importance of community networking provide valuable tools for anyone looking to navigate the Chicago real estate scene.
AI Snips
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Transcript
Episode notes
Confirm Suburban Rental Permits
- Check local rental license and inspection rules before renting suburban properties to avoid permit issues.
- Pull permits for visible work (HVAC, copper, AC) or risk retroactive enforcement during inspections.
AI Multiplies Deal-Filtering Capacity
- AI can scale deal screening by ingesting incoming deal data and scoring properties against trained parameters.
- With good inputs (spreadsheets/emails) the automation filters hundreds of deals and surfaces the 10% worth pursuing.
Develop Automations In Small Phases
- Build automations in small phased modules rather than one large system to reduce breakage and simplify debugging.
- Add features iteratively and plan fallbacks so single logic changes don't break the whole workflow.
