Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars
Release Date: 08/07/2025
Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Micah White is a real estate coach with a proven track record of finding cash flowing real estate with great ROI! Micah starts by explaining the ins and outs of his first couple house hacks in Logan Square and North Lawndale. He provides great pointers on proper due diligence to...
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Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Paul de Luca of The Axon Group joins us to provide great insights on leveraging house hacking to grow a portfolio and how to succeed as an investor-friendly real estate agent! Paul jumps right into the nitty gritty of his first couple house hack deals! He gives tips on getting off...
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Episode 397: When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property?
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= What are the "do's" and "don'ts" when filing an insurance claim? ============= Connect with Mark and Tom: Email the Show: Guest: Josh Steigelmann, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Fernando Angelucci returns to the podcast to explain how he has rapidly grown his self storage business and the drivers behind increasing self storage demand! Fernando explains his marketing strategy to optimize deal flow despite the low inventory environment. He delves deep into...
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Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Max Motew, Director of Leasing at Mo2 Properties, joins us to share great insights on acquiring, renovating, and stabilizing small multifamily properties in Chicago’s north side! Max jumps right in by sharing top considerations when renovating Chicago landmarked properties! He...
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Episode 394: The Legal Nuances of Different Real Estate Partnership Structures
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= What do investors need to consider from a legal perspective when setting up new partnerships? ============= Connect with Mark and Tom: Email the Show: Guest: Bibek Das, ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 393: Chicago Veterans’ Guide to Real Estate Success with DuBois Toy
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= DuBois Toy is a seasoned real estate investor, veteran, and cybersecurity analyst who has a passion for helping veterans maximize their real estate benefits! DuBois kicks things off by discussing his start in real estate which involved a house hack and dealing with an eviction! He...
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Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Kevin Cawley, aka Cost Seg Kev, is a Senior Account Executive at CSSI Services - a firm with over 55,000 cost segregation studies completed since 2003. Cost Seg Kev starts by reviewing the 101 on cost segregation and how it can be used to offset your tax liability. He dives into...
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Episode 391: Do You Have a Business Continuation Plan?
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Josh Steigelmann explains the importance of a business continuation plan and provides step-by-step guidance on how investors can set-up a business continuation plan ============= Connect with Mark and Tom: Email the Show: Guest: Josh Steigelmann, Link: ----------------- ...
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Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims
Straight Up Chicago Investor
Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Mitch Schoeneman is a Managing Partner at A. Schoeneman & Co. - a top rated Chicago public insurance adjusting firm that has been serving customers for over 55 years! Mitch starts by explaining the services rendered by insurance adjusters. He breaks down how investors can set...
info_outlineProperties for Sale on the North Side? We want to buy them. Email: [email protected]
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
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Kevin Cawley, aka Cost Seg Kev, is a Senior Account Executive at CSSI Services - a firm with over 55,000 cost segregation studies completed since 2003.
Cost Seg Kev starts by reviewing the 101 on cost segregation and how it can be used to offset your tax liability. He dives into the benefits of real estate professional status and recent tax code changes by the presidential administration. He also touches on frequently asked questions on cost segregation studies and closes with how he built his business and reputation!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
Guests: Kevin Cawley, CSSI Services
Link: CSSI Cost Segregation Calculator
Link: SUCI Ep 59 - Cost Seg Kev
Link: James Mahon (CPA Referral)
Link: At Your Command (Book Recommendation)
Guest Questions
02:46 Housing Provider Tip - Go above and beyond to acknowledge tenants after management mistakes.
05:00 Intro to our guest, Cost Seg Kev!
05:43 The 101 on Cost Segregation.
11:37 The benefits of real estate professional status!
25:42 Recent changes to depreciation rules.
32:15 Technical side of cost segregation!
34:23 Cost Seg on smaller properties.
43:43 What is your competitive advantage?
44:42 One piece of advice for new investors.
46:00 What do you do for fun?
46:37 Good book, podcast, or self development activity that you would recommend?
47:52 Local Network Recommendation?
48:55 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.