Straight Up Chicago Investor

SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down everything you need to know about architectural plans and permits in Chicago! Tom discusses when you need plans and permits for a project and when it's appropriate to engage an architect. He shares the best way to optimize timelines to ensure your plans and permits get approved as fast as possible. Tom discusses lessons learned on design and functionality particularly on luxury redevelopments! He closes with insights on dormer additions and considerations for ADUs and historic district remodels that will add to your permit approval timeline! 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: Tom Shallcross, Straight Up Chicago Investor Link: SUCI Ep 235 - Tom Shallcross Guest Questions: 02:32 Housing Provider Tip - Understand 2026 leasing law changes regarding minors on leases! 04:33 Intro to our guest, Tom Shallcross! 05:35 The process of developing plans and permitting. 14:11 Top design and functionality mistakes! 16:16 Must-have amenities in luxury remodels. 20:40 Timeline for creation of architectural drawings. 27:23 The role of expeditors. 35:29 Design considerations for dormer additions. 41:40 What do you do for fun? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

How do I navigate the rent determination process for Section 8 applicants in Chicagoland? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Zeke McDonald-Lewis is an attorney at Erwin Law who specializes in real estate evictions and civil litigation! Zeke starts by breaking down the first steps in handling a non-paying tenant including the appropriate steps for delivering a 5-day notice. He gets granular on the eviction process timeline and dos/don'ts to avoid delaying the process. Zeke shares top mistakes made in eviction cases and shares horror stories caused by those mistakes! He closes best practices to handle squatters and an outlook on potential changes to the eviction process. 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: Zeke McDonald-Lewis, Erwin Law Link: Zeke's LinkedIn Link: SUCI Ep 330 - James Erwin Link: Red Rising (Book Recommendation) Guest Questions: 03:50 Housing Provider Tip - Plan tenant payment plans to clear balances quickly! 05:51 Intro to our guest, Zeke McDonald-Lewis! 12:25 First step in dealing with a non-paying tenant. 19:54 Next steps after serving a 5-day notice. 34:18 Timelines for the eviction process. 38:36 Top eviction mistakes. 44:43 Eviction horror stories! 47:25 Dealing with squatters. 51:01 Zeke's outlook on the eviction process! 55:02 What is your competitive advantage? 55:54 One piece of advice for new investors. 56:31 What do you do for fun? 56:59 Good book, podcast, or self development activity that you would recommend? 57:15 Local Network Recommendation? 58:00 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Niko Apostal, founder of Niko Collaborative and managing broker at Essex 312, joins us to share his expertise in real estate brokerage with a focus on 2-4 unit buildings! Niko starts by explaining how he got his real estate business off the ground in the early 2000s and survived the real estate crash! He provides practical tips for anyone looking to start a real estate business. Niko shares details on his first 2-unit building in Logan Square and dives deep into top "gotchas" when purchasing 2-4 unit buildings. He closes with a bullish outlook on Chicago particularly the areas surrounding the United Center! 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: Niko Apostal, Niko Collaborative - Essex 312 Link: The ONE Thing Podcast Link: The Power of Full Engagement (Book Recommendation) Link: SUCI Ep 112 - Chicago Cityscape Guest Questions: 01:58 Housing Provider Tip - Be sure to appeal property taxes particularly with upcoming reassessments! 03:36 Intro to our guest, Niko Apostal! 08:41 Weathering the storm of the real estate crash! 20:53 Lessons learned and tips for starting a real estate brokerage. 30:25 Investing in a 2-unit in Logan Square. 42:00 Essex 312 vs Essex Realty Group. 48:50 Gotchas when buying a 2-4 unit building! 52:10 Neighborhoods that Niko is bullish on! 60:20 5 Year Outlook on Chicago. 62:24 What is your competitive advantage? 63:11 One piece of advice for new investors. 63:27 What do you do for fun? 63:39 Good book, podcast, or self development activity that you would recommend? 64:04 Local Network Recommendation? 64:57 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

How do I protect myself against potential tenant screening scams? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast 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 ============= Link: Forewarn.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Lawrence starts by explaining how he found his business niche and lessons learned from working with successful developers. He gets granular on his geographical areas of focus and on understanding risks when developing product that will set the top comparable in a neighborhood. Lawrence provides a great take on his top Chicago neighborhoods for upside and reasoning for why he is bullish. Throughout this episode, Lawrence emphasizes the importance of deeply understanding your market and getting in the game to achieve success! 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: Lawrence Dunning, Fulton Grace Realty Link: SUCI Ep 118 - Lawrence Dunning Link: Enter The Lionheart (Lawrence's Podcast) Link: The One Thing (Book Recommendation) Link: Vevor Adjustable Handrails Guest Questions: 03:01 Housing Provider Tip - Leverage adjustable handrails for an affordable solution to meet compliance requirements! 04:58 Intro to our guest, Lawrence Dunning! 12:27 Lawrence's business and areas of focus! 16:40 Real estate agent's value to developers. 26:33 Setting the top comparables in a neighborhood. 35:02 Lawrence's top emerging neighborhoods! 45:46 Outlook on Chicago's south side. 52:01 What is your competitive advantage? 53:00 One piece of advice for new investors. 53:47 What do you do for fun? 54:54 Good book, podcast, or self development activity that you would recommend? 56:43 Local Network Recommendation? 57:02 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs! Mark jumps right in by giving a bit of history on why rental licenses were originally introduced. He gets granular on various village requirements for rentals including smoke detectors, GFCIs, and hot water heaters. Mark explains some hoops you can expect to jump through during Point of Sale inspections and how to expedite the process! He closes by breaking down tax transfer stamps and other transaction fees in the Suburbs so you can accurately factor this into your holding costs! 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: Mark Ainley of GC Realty & Development Link: Mark's Instagram Link: The Science of Scaling (Book Recommendation) Link: It's How We Play The Game (Book Recommendation) Guest Questions: 03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up! 03:16 Housing Provider Tip - Understand the updated CARES Act notice requirements! 04:55 Intro to our guest, Mark Ainley! 05:48 The history of village requirements for rentals. 09:17 Considerations when investing in Schaumburg. 17:27 Insights on permits and associated fees. 21:38 Navigating point of sale inspections in different villages. 31:46 What to know about tax transfer stamps! 35:56 Overview on rental licenses, village inspections, STR licenses, and more! 39:51 Book recommendations from Mark! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

When do I have to have my cost segregation done to ensure it is good for my 2025 taxes? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Cost Seg Kev from CSSI 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 ============= Link: Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Luke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio. Luke kicks things off by sharing how he acquired his first house hack and provides insights on the ADU process that he used to add a third legal unit. He lays out top considerations when converting a basement into a dwelling unit including the top dollar items. Luke talks about getting a 4-unit acquisition to the finish line, despite it involving violations and a difficult seller. Throughout this episode, Luke demonstrates how holding real estate for the long term has built him great wealth and how staying active in the market is the key to success! 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: Luke Helliker Link: Luke Helliker - DocuSign | LinkedIn Link: EUBA Link: SUCI Ep 345 - Joey Turano Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon Link: SUCI Ep 389 - Sebastian Mysliwiec Link: Rich Dad Poor Dad (Book Recommendation) Guest Questions: 03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up! 05:03 Intro to our guest, Luke Helliker! 13:19 Luke's first deal: a 2-unit house hack! 20:18 How to leverage the ADU process. 27:20 Funding an ADU project. 41:09 Navigating investing with your significant other. 43:15 Acquiring a 4-unit building in a competitive market! 58:47 Lessons learned on the 4-unit acquisition. 65:30 Luke's next investment targets. 66:19 What is your competitive advantage? 67:15 One piece of advice for new investors. 67:59 What do you do for fun? 69:19 Good book, podcast, or self development activity that you would recommend? 70:01 Local Network Recommendation? 70:30 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Shawn Good is a seasoned attorney and real estate investor with vast experience acquiring and stabilizing off-market real estate. Shawn kicks things off by discussing his first few deals which included a condo and an 8-unit building. He shares some funny stories on unfair partnerships he's been a part of and important points on due diligence when acquiring a property. Shawn explains how joining Collective Genius helped him take his law practice and direct to seller marketing to the next level. He closes with his 5-year plan and hilarious real estate horror stories! 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: Shawn Good, Good Law Group Link: SUCI Ep 292 - Dorian Bezanis Link: The Collective Genius Podcast Link: The Charisma Myth (Book Recommendation) Guest Questions: 02:06 Housing Provider Tip - Ensure to have a lease on a departing residence when required for another loan! 04:03 Intro to our guest, Shawn Good! 08:25 Transitioning to an 8-unit building after a condo purchase. 13:38 House hacking and starting a law practice! 21:23 Simple partnership structures. 26:28 Generating off-market deal flow! 36:36 Shawn's 5 year plan. 46:44 Horror stories! 51:37 What is your competitive advantage? 52:18 One piece of advice for new investors. 53:27 What do you do for fun? 53:50 Good book, podcast, or self development activity that you would recommend? 55:00 Local Network Recommendation? 56:54 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.