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How to Invest in DuPage County with Katie and Rob Hayes

192 views· 9 likes· 66:53· Jul 10, 2025

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Episode 386: How to Invest in DuPage County with Katie and Rob Hayes Katie and Rob Share why you don’t need to do as much as you think.. their lessons learned! Buy and Hold, Cash Flow, Western Suburbs, Short-Term Rentals, Rehab Katie and Rob Hayes are investors and realtors with nearly 2 decades of experience acquiring and managing investment properties! The duo starts by sharing their background including investing in Florida before transitioning to the Chicago Western Suburbs. They share lessons learned from investing in lower cost areas and why they pivoted to higher class assets. Rob and Katie share golden nuggets on marketing to owners for deal flow and on operating short-term rentals. They close out with a positive outlet on Downer’s Grove and why investors should be considering it! 00:00 – Farming neighborhoods and using maps to find off-market rentals 06:28 – First profitable flip and transition into long-term rentals 13:00 – C-class properties vs. A/B-class suburban rentals 24:55 – Leaving W-2 jobs and going full-time into real estate 29:44 – Driving for dollars and door-to-door lead generation 39:17 – Scaling down: fewer properties, more control and cash flow 44:32 – How much Airbnbs make in Downers Grove vs. traditional leases 50:06 – Navigating local zoning laws for short-term rentals 53:27 – Backup plans: converting short-term rentals to long-term leases 58:55 – Advice for first-time suburban rental property investors Join us as we share our winning strategies, success stories, obstacles we've encountered, and most importantly, the lessons we have learned along the way. If you are ready to learn the ins and outs of the investing in Chicago and suburbs. SUBSCRIBE: http://ow.ly/pNzU50BFJtU Got an idea for the show? Shoot us an email at straightupchicagoinvestor@gmail.com Follow us behind the scenes on Instagram: http://ow.ly/lquy50BGadL Make our acquaintance on our Club: http://ow.ly/RZvr50BGaei Give us a shout on Facebook: http://ow.ly/Qqr350BGaeM Visit our world directly: https://www.straightupchicagoinvestor.com/ Listen to the 𝗦𝘁𝗿𝗮𝗶𝗴𝗵𝘁 𝗨𝗽 𝗖𝗵𝗶𝗰𝗮𝗴𝗼 𝗜𝗻𝘃𝗲𝘀𝘁𝗼𝗿 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 on your favorite streaming service: http://ow.ly/lI7050BGafp

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