Straight Up Chicago Investor

Zack Limbaugh, an attorney who handles Chicago building code and municipal enforcement, returns with practical intel. He covers buying properties with violations, lender challenges, due diligence tactics like maps and FOIA, common tickets to watch for, demo court risks, and how to manage fines and compliance timelines.

Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career! Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to create equity! Zach gives property management insights for house hackers which are centered around doing right by tenants and people in general. He explains the ins and outs of acquiring a property by assuming a VA loan. Throughout the episode, Zach demonstrates that growing a portfolio as a busy professional is doable and that the financial reward far outweighs the work that is required! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Zach Posey, Chicago Multifamily Club Link: Chicago Multifamily Club Meetup Link: Wisdom Takes Work (Book Recommendation) Link: SUCI Ep 52 - Aaron Zimmerman Link: SUCI Ep 326 - RJ de Leon Guest Questions: 01:58 Housing Provider Tip - Understand easy fixes for malfunctioning garbage disposals! 03:57 Intro to our guest, Zach Posey! 07:38 Starting off with a 4-unit house hack. 17:25 Acquiring a second house hack in Roscoe Village. 26:28 Property Management tips for house hackers! 28:44 Leveraging assumable loans to make the numbers pencil. 34:41 The value of networking events. 37:40 Zach's REI goals and outlook on Chicago! 42:42 What is your competitive advantage? 43:13 One piece of advice for new investors. 43:35 What do you do for fun? 43:50 Good book, podcast, or self development activity that you would recommend? 44:40 Local Network Recommendation? 45:39 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

What is real estate professional status and why is it important for investors? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Michael Procaccio, Pro Financial Services Group Inc Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Reed Meyer, founder and managing broker at Lease312, shares top tier leasing advice and how connecting with mentors has propelled his real estate journey's growth at such a young age! Reed starts off by detailing the process of acquiring his first property; a 3-unit house hack in Logan Square. He talks about purchasing an industrial warehouse and flipping it for double the price in just 45 days! Reed shares golden insights on apartment listing marketing, leasing, and tenant expectations in prime North Side neighborhoods. To conclude, Reed gives a 5 year outlook on his business goals and Chicago's residential rental market! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Reed Meyer, Lease312 Link: Reed's LinkedIn Link: SUCI Ep 421 - Alec Greenberg Link: SUCI Ep 259 - Sal Becovic Link: SUCI Ep 22 - Matt Fritzshall Link: SUCI Ep 51 - John Westbrook Link: Gabe Horstick (Network Referral) Link: Zeckendorf Autobiography Guest Questions: 01:56 Housing Provider Tip - Get great pictures, get floor plans, and be responsive to optimize leasing of apartments! 03:15 Intro to our guest, Reed Meyer! 06:45 Reed's first house hack. 11:37 The nuances of industrial property investing. 16:40 Reed's transition from corporate to real estate full time! 22:12 Top leasing mistakes by landlords. 29:15 Jumping into a 5-unit house hack! 34:00 Tenant expectations in Lakeview. 40:50 Outlook on the Chicago leasing market and rent growth! 42:52 Reed's 5 year business outlook. 45:43 What is your competitive advantage? 45:53 One piece of advice for new investors. 46:10 What do you do for fun? 46:54 Good book, podcast, or self development activity that you would recommend? 47:26 Local Network Recommendation? 48:08 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Darryl Jacobs, partner at Ginsberg Jacobs, has over 3 decades of experience in tax and corporate law with a focus on tax credit financing transactions. Darryl starts off with a high-level overview of the various tax credits available to investors. He dives deep on opportunity zones and how geographical areas get designated as opportunity zones. Darryl explains how investors can leverage New Markets Tax Credits. Throughout the show, Darryl demonstrates his deep knowledge in Tax Credits and conveys how it can be a super powerful tool for investors who know how to leverage it! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Darryl Jacobs, Ginsberg Jacobs Link: Sonny Ginsberg (Network Referral) Link: SUCI Ep 26 - Neal Bawa Guest Questions: 01:49 Housing Provider Tip - Ensure proper transfer of utilities when purchasing a property to avoid outages! 04:09 Intro to our guest, Darryl Jacobs! 13:26 Understanding Opportunity Zones. 25:04 Opportunity Zones 1.0 vs 2.0! 32:14 New Markets Tax Credits. 54:48 Other tax credit resources for investors. 59:55 What is your competitive advantage? 62:48 One piece of advice for new investors. 64:11 What do you do for fun? 64:37 Good book, podcast, or self development activity that you would recommend? 65:33 Local Network Recommendation? 66:02 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Updates to the 2026 lease disclosure and tenant rights for domestic violence are explained. New rules on lock changes, who pays, and tenant-proof options are discussed. Changes to squatter laws and police response are reviewed. Guidance on documents for police, using immediate demand notices, and process-server best practices is covered.

Mike Scanlon, Chicago broker/investor with tax and finance expertise. Jake Fugman, Chicago broker/investor focused on multifamily deals and market strategy. They reflect on 2025 office and downtown trends, debate mortgage reforms like portable or long‑term products, unpack Chicago ADU expansion challenges, and assess interest rate drivers and brokerage platform shifts for 2026.

Jessica Erickson, Director of Economic Development for the City of Woodstock, joins us to discuss development news and opportunities in Woodstock, IL! Jessica starts with her backstory on moving from Denver to Chicagoland and ultimately taking a role in Economic Development for the City of Woodstock. She breaks down Woodstock's downtown redevelopment plan and also speaks to city corridors with development opportunities. Jessica explains "infill" sites, metrics for successful developments, and strategic planning of developments to allow for future adaptive reuse. Throughout the show, Jessica demonstrates a passion for sustainable developments that enhance the quality of life for the residents of Woodstock! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Jessica Erickson, City of Woodstock Link: Jessica's LinkedIn Link: Woodstock Comprehensive Plan Link: The Prof G Pod (Podcast Recommendation) Link: Heartland Realtor Organization (Network Referral) Guest Questions: 02:13 Housing Provider Tip - Utilize water shut off valves at vacant properties to prevent issues! 03:52 Intro to our guest, Jessica Erickson! 09:14 Jumping into Economic Development in Woodstock, IL. 16:50 Woodstock's downtown redevelopment plan. 23:44 Breaking down "infill" sites. 25:54 Measuring successful developments. 29:28 Redevelopment opportunities in Woodstock. 31:27 Future-proofing development sites. 38:41 Closing remarks on the upside of Woodstock! 43:12 Woodstock's competitive advantage? 43:39 One piece of advice for new investors. 44:33 What do you do for fun? 44:55 Good book, podcast, or self development activity that you would recommend? 45:48 Local Network Recommendation? 46:16 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Benjamin Stef, mortgage pro and founder of Funding Freedom, breaks down HELOC and DSCR line-of-credit options for real estate investors. He explains quick no-appraisal HELOCs and specialized DSCR HELOCs for LLC-held rentals. Listeners hear timelines, rate and term differences, draw rules, LTV limits, and practical use cases for short-term financing and scaling portfolios.

Ryan Smith, top producing agent specializing in REO properties, returns to provide an update on the state of the Chicagoland foreclosure market heading into 2026! Ryan starts with an overview on the foreclosure process and expectations when getting into a foreclosure transaction as a buyer. He provides tips on positioning yourself as a legit, experienced buyer in the eyes of REO listing agents. Ryan gets granular on latest foreclosure statistics and provides his outlook on the REO market heading into 2026. He closes with his take on Chicago's crime problem and the neighborhoods that he is bullish on! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Ryan Smith, RE/MAX Properties Link: Ryan's Instagram Link: SUCI Ep 70 - Ryan Smith Link: SUCI Ep 28 - Ryan Smith Link: The Chicago Way (Podcast) Link: DAWGS Vacant Property Security Guest Questions: 02:05 Housing Provider Tip - Understand manufacturer warranties on appliances and reconsider extended warranties! 04:15 Intro to our guest, Ryan Smith! 10:47 Risks associated with buying properties at the auction. 13:12 Understanding properties in receivership. 15:55 Expectations on REO transactions! 25:15 Key Foreclosure Statistics! 35:54 Ryan's outlook on the foreclosure market. 42:55 Promising south and west side neighborhoods. 46:19 Solving Chicago's largest issues. 47:20 What is your competitive advantage? 48:12 One piece of advice for new investors. 49:20 What do you do for fun? 49:50 Good book, podcast, or self development activity that you would recommend? 50:45 Local Network Recommendation? 51:51 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.