Straight Up Chicago Investor

Many fear what they don't understand. That's exactly why we put together this round table discussion with two other great CHA section 8 property managers. Listen in as we address the entire workflow from screening the applicants, to the move in, and everything that happens in between. Section 8 can be a great investment strategy, but it's imperative you understand how it works...ESPECIALLY in a city like Chicago. If you learned something today, please leave us a review and share us with a friend. Enjoy the episode! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jared Kott (Email: Jared.kott@marblestonepg.com) and Eric DeLeon (Email: Office@philtonllc.com) of Chicago Section 8 Sponsor: Appeal.tax and Showdigs Link: HCV Inspections Link: Mobility Counseling Program Link: BiggerPockets: Real Estate Investing Community & Advice Link: One Rental At A Time: The Journey to Financial Independence through Real Estate Link: Chicago Section 8 Housing Resources ----------------- Guest Questions Jared, How do you respond to questions about accepting section 8 tenants? 9:00 Screening section 9:40 Eric, how do you screen section 8 tenants? 9:40 How do you account for utility costs with section 8? 11:20 Rent burden worksheet collection 14:40 How do extra costs like pets or garage get accounted for? 17:25 Paperwork question section 21:25 Best practices for submitting paperwork to the CHA? 22:30 Inspection section 30:45 Wrap Up Questions What are some best practices for inspection day? 31:30 What are some common fails on the initial inspection that can be avoided? 34:30 What are "emergency fails"? 44:00 What is rent abatement? 44:50 What is the typical timeline of a section 8 tenant? 49:00 What is the mobility program? 51:30 What is one piece of advice you'd tell someone who has never purchased sec 8? 53:44 What do you do for fun? 54:50 What is a good self development activity you'd recommend? 55:20 Who is one person you'd recommend? 56:20 That's our show! Thanks so much for listening! If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

It's March and taxes are top of mind! However, by only reactively focusing on taxes during this one part of the year, you are potentially leaving money on the table. Aaron Zimmerman, a Chicago investor and CPA, provides great insights into how to best work with a CPA, the importance of maintaining good records, overlooked deductions, and proactive measures to maximize your net worth. Aaron also explains why it's important to understand the difference between capex and general maintenance come tax time. And why your accountant should break out their bill for you at the end of it, because yes, even that makes an impact. Lastly, he also covers the nuances of maximizing your return as a househacker. Listen in and let us know what you think! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Aaron Zimmerman of Lipschultz, Levin & Gray Sponsor: John Warren of Second City Real Estate Sponsor: Appeal.tax Link: MileIQ - Automatic Mileage Tracker - Deductions & Reimbursements Link: QuickBooks®: Official Site | Smart Tools. Better Business. Link: Stessa: Smart Accounting Software for Rental Property Landlords Link: Joe Fairless's Podcast | The Best Ever Real Estate Show ----------------- Guest Questions Landlord tip of the week 3:10 What is the difference between an accountant and a CPA? 6:00 What are some things you talk about when you talk to a new client? 6:45 What are some things an investor might do differently when trying to be tax smart? 8:00 What is depreciation in terms of real estate? 8:30 What tax laws came out in 2017 that allow for bonus depreciation? 9:50 What are the categories of expenses I should have categorized for a CPA? 11:00 What is a schedule E and where is it located? 12:35 How should an investor keep track of expenses for taxes? 14:00 What are some good softwares to help with bookkeeping? 16:15 What are some of the biggest things investors miss when they do taxes? 18:20 How is lost rent accounted for? 23:00 What are some nuances with house hacking compared to a traditional investment? 25:45 What are some write offs new real estate professionals can take? 27:15 What are some good things I should ask when interviewing accountants? 32:10 What are some red flags that get the attention of the IRS? 34:10 Wrap Up Questions What is your competitive advantage? 37:45 What is one piece of advice you'd give a new investor? 38:40 What do you do for fun? 38:50 What is a good self development activity you'd recommend? 39:10 Network recommendation? 39:30 How can we learn more about you? 40:00 That's our show! Thanks so much for listening! If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Would you trade salary for knowledge? John Westbrook spent time straight out of college working for one of Chicago's largest property managers to build-up his foundational knowledge of the industry. John has since transformed this knowledge into a substantial portfolio of multifamily buildings on the Northside. John explains how he plans for the long-term with his rehabs, appreciates previously gutted buildings, and focuses on the end users experience to differentiate his investments (it's much more than numbers on a spreadsheet). John also shares the importance of finding mentors and how his partnerships have catapulted him to success. If you enjoy today's episode, please leave us a review and share us with someone who may also find value in this content. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: John Westbrook of Logan Square Real Estate Broker | @properties Sponsor: ShowDigs Sponsor: Appeal.tax Monthly Tip: Renovo Financial Link: Luke Blahnik - Chicago Real Estate Broker | @properties Link: Muros | A Global Art Activation Agency Link: Bigger Pockets Link: The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It ----------------- Guest Questions Intro. 9:30 What are some key things you learned while working for such a large landlord? 13:20 Did you ever consider buying smaller buildings rather than larger buildings? 14:30 What are some neighborhoods you're active in? 16:00 What are you looking for on a deal in Humboldt Park? 17:45 When you got artwork commissioned, did you need to get permissioned for it? 25:30 What would you tell someone who owns a 3 unit in terms of financing? 32:10 Walk us through this large multi family. 33:50 How do you estimate how long it will take to rehab a large building? 38:20 What can you tell us about west humboldt park? 42:30 Wrap Up Questions What is your competitive advantage? 45:33 What is one piece of advice you'd give to a new investor? 46:23 What do you do for fun? 47:30 What is a good self development activity you would recommend? 49:20 Quality resource 50:10 How can we reach you? 50:50 That's our show. Thanks for listening to another great episode! If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

For our 50th episode we thought we'd give everyone a special treat... Andrew Holmes is one of the most well-known names in Chicago Real Estate Investing. Andrew explains his incredible journey, from his early days as a hustling agent, to how he structured his first few investment deals. Andrew dives into specifics on how he finds deals, what attributes he looks for in an investment property, how he underwrites properties, and how he teaches others to scale. There is so much to break down here it's an episode you'll need to listen twice! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Andrew Holmes of Andrew Holmes Real Estate Sponsor: John Warren of Second City Real Estate Sponsor: Appeal.tax Link: The Intelligent Investor Link: National RE Invest ----------------- Guest Questions Guest Introduction 7:20 When you were a young agent, what separated you from the crowd? 8:40 How did you pivot from real estate agent to real estate investing? 13:10 How did you scale during 2008? 15:30 How are you doing this today with your students? 22:50 What are some strategies you teach students? 27:30 How are you suggesting students to underwrite for the soft costs? 31:50 How are you teaching students to buy properties in this competitive environment? 40:00 Why do you prefer single family over multifamily? 42:45 How are you accounting for some of the issues around the Chicagoland area? 45:20 How did you start and grow Chicago REIA? 47:20 Wrap Up Questions What is your competitive advantage? 50:00 What is one piece of advice you'd give to a new investor? 50:40 What do you do for fun? 51:35 What is a good self development activity you'd recommend? 52:20 Who is one person you'd recommend from your local network? 54:40 How can we learn more about you? 55:50 That's our show. Thanks for listening to another great episode! If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

For the past 15+ years, Rosario Terracciano has been cutting his teeth with a lot of hard learned lessons. In today's episode, he shares some early mistakes he made about buying, working with contractors, estimating ARVs and leasing. He shares how he weathered the sub-prime crisis and emerged stronger - co-founding Clickinvest and ultimately representing banks and buyers in more than $300 million of real estate transactions . Some of the big industry shifts that took place during the sub-prime crisis are still at play today and he Roario provides strategies to prepare and thrive if another downturn hits. If you enjoyed listening to today's episode, please leave us a 5 star review and share us with a friend. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano of Clickinvest Sponsor: ShowDigs Sponsor: Appeal.tax Link: The Power of Positive Thinking: Peale, Dr. Norman Vincent Link: Workman Lending Team Link: deals@clickinvest.com | rosario@clickinvest.com ----------------- Guest Questions Landlord tip 3:25 About Rosario 5:20 What does it mean to "buy wrong?" 8:10 What was your exit strategy on the bad mistakes? 13:30 What was your next move after foreclosure? 17:20 Did you just focus on Chicago? 21:30 What would you say to an investor interested in working with an REO agent? 22:30 How has institutional money changed the investing landscape? 32:40 How does an individual investor capitalize on the institutional strategy? 36:45 What is the benefit to working with click invest? 43:20 How are the click invest deals financed? 46:20 Wrap Up Questions What's your competitive advantage? 48:20 What is one piece of advice you'd give a new investor? 49:45 What do you do for fun? 51:35 Self development activity? 52:15 Who would you recommend as a quality resource? 53:15 How can we learn more about you? 53:50 Chicago fact 54:45 That's our show. Thanks for listening to another great episode! If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

For everyone working a W2 job, our guest today, David Shifrin, is a great example of how to incorporate real estate into your long-term plan without having to give up your current career. David Shifrin wanted a way to marry his professional career as a plastic surgeon to his interests in becoming a real estate investor. This path led him to Motor Row and an acquisition of a historic Chicago building. Listen as he describes why he is bullish Motor Row and the lessons he learned as he simultaneously built two businesses from the ground up right on Motor Row. If you like what you hear today, share us on Facebook and tag us with what you found most interesting. If you want to see how we can improve your properties performance, reach out to us at GCRealtyInc.com. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: David Shifrin of David Shifrin MD Sponsor: John Warren of Second City Real Estate Sponsor: Appeal.tax Link: Am I Being Too Subtle?: Straight Talk From a Business Rebel Link: Evergreen Bank Group | Oak Brook, Evergreen Park, Hinsdale, IL Link: Mike Chock on LinkedIn Link: Robert Sikkel | Goose Island Real Estate Broker | @properties Link: David Shifrin MD | Chicago Plastic Surgeon ----------------- Guest Questions Landlord tip of the week 4:20 Guest Intro 7:15 What excited you about investing in real estate? 8:00 Why did you decide to go down the hands on approach rather than a syndication? 9:00 Description of motor row? 10:30 Was the building vacant when you bought it? 13:00 What types of challenges did you have when you took on this project? 14:00 Can you explain TIF funding? 16:40 Did you know you were investing in a historical district and the challenges that presents? 20:00 Can you explain cost segregation? 21:30 While you were doing the work on your building, are you continuing to look at other deals? 25:50 What's your primary strategy for searching for buildings? 27:30 Wrap Up Questions What is your competitive advantage? 32:30 What is one piece of advice you'd give to a new investor? 33:30 What do you do for fun? 34:09 What is a good self development tool you'd recommend? 34:40 Name one person you'd recommend as a good local resource? 36:37 How can we learn more about you? 37:25 Chicago Fact 38:05 Thanks for listening! Give us your feedback, give us your ideas for what should be on the show; we love hearing what you want and we are listening. If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

The term "1031 Exchange" is ubiquitous, but do you really know what it is or how to even engage in one? Lauren Speidel of Exeter1031 is a subject matter expert and breaks it down for you today. She'll explain the different parties involved, what the criteria are and what you need to know before having the necessary conversations. Our hosts, Tom and Mark, have great FAQs for Lauren and she delves into a lot of content on one of our most informative episodes yet. If you like what you hear today, share us on Facebook and tag us with what you found most interesting. If you want to see how we can improve your properties performance, reach out to us at GCRealtyInc.com. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Lauren Speidel of Exeter 1031 | Connect with Lauren on LinkedIn Sponsor: John Warren of Second City Real Estate Sponsor: Appeal.tax Link: The Exeter Group Launches Go Ahead, ASK! Podcast Link: Mandy McAllister Link: Exeter 1031 on Facebook ----------------- Guest Questions Guest Intro 6:20 What is a 1031 exchange? 7:15 What is a "like property" and how do you define it? 9:25 What is an intermediary and what happens before and after a closing? 13:15 What are some questions you should ask an intermediary? 14:55 How does the purchase of a new property differ from a regular closing when in a 1031 exchange? 21:32 Can I wrap a whole portfolio into a single 1031? 22:45 How does househacking fit into a 1031 exchange? 24:20 What can you do with a vacation rental or second home when it comes to a 1031? 28:50 Do you have conversations with clients' CPAs? 30:20 Is there a minimum dollar threshold you recommend clients have before it makes sense? 33:15 Can 1031 Exchanges work when an entity wants to split after a closing and put the proceeds in a new entity? 34:00 What are the time limits on seasoning and intent to hold? 37:00 What are the estate planning benefits to 1031 exchanges? 38:00 What is a reverse 1031 exchange? 40:45 Wrap Up Questions What is your competitive advantage? 43:00 What advice would you give someone who is about to sell in Chicago? 44:00 What do you do for fun? 44:35 What is a good self development activity you'd recommend? 45:20 Is there any way we can provide value to you or learn more about you? 46:50 Thanks so much for listening. Please share this with a friend and leave us a 5 star review. Thank you so much for listening. As always, we're here to help YOU. If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Chicagoland is an enormous market with a ton of sub markets. Anthony Citriglia of Essex Realty's submarket covers many of the near north and near northwest suburbs and he breaks down exactly what those markets are like; how they differ from Chicago; and how they differ from each other. Following the post-war boom, cheaper access to cars, and the development of several Metra lines, the 50s-80s were filled with tons of development, mostly still currently owned by mom & pop landlords. Find out what it takes to succeed in these markets as Anthony drops street-level knowledge including typical price-per door, dividing lines where this pricing adjusts, tenant expectations, and the physical housing stock. If you want to improve your own tenant performance, give GC Realty a call and visit our website at https://www.gcrealtyinc.com/ Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Anthony Citriglia of Essex Realty Group Link: Brian Kochendorfer Link: Brian Karmowski Link: Kevin Cawley - Senior Account Executive - Cost Segregation Services, Inc. ----------------- Guest Questions Landlord tip of the week 3:00 What markets do you focus on? 6:30 What is the market environment in Niles? 7:25 Is there a difference whether you're on the East or West side of Milwaukee in Niles? 8:30 How do property taxes change when you jump over the city limits? 9:35 When someone says they want to invest, how do you answer that? 11:00 How are prices different between Niles and Skokie? 11:50 What is the opportunity like in Evanston compared to Skokie? 14:45 What is the housing stock in the north suburbs? 15:30 What is something people should be aware of when investing in the north suburbs? 16:10 How does the northwest market differ from the north suburbs? 17:45 What is the housing stock like of the near northwest suburbs? 21:35 How important is it to be close to the NW metra line? 21:55 Is there opportunity for deals in the NW suburbs? 23:20 What are some problems buyers are seeing when properties are under contract? 29:30 What is a california style building and how do those trade? 32:50 Wrap Up Questions What is your competitive advantage? 33:40 What is one piece of advice you'd give a new investor? 34:25 What do you do for fun? 35:00 Who would you recommend and a quality resource? 36:05 How can we learn more about you? 37:12 Thanks so much for listening. Please share this with a friend and leave us a 5 star review. Thank you so much for listening. As always, we're here to help YOU. If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

For over 35 years, Jack Crane has been providing expertise on financing the acquisition and rehabilitation of commercial real estate. The majority of those years have been spent as Sr. VP of lending at CIC where he is responsible for carrying out the mission to be a leading force in both neighborhood revitalization and affordable housing. From lending during tough times, to helping analyze risk, Jack explains how CIC has played a predominant role over multiple decades in transforming Chicagoland neighborhoods. Jack also describes how you as an inverter can benefit from CIC's lending programs and experience to better rehab and finance your next investments. If you like what you hear, please share us with a friend and leave us a 5 star rating. Lending Tip of the Month brought to you by Renovo Financial - https://www.renovofinancial.com/ Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jack Crane of Community Investment Corporation Monthly Tip: Renovo Financial Link: Troubled Building Initiative (TBI) Link: Elevate Energy Link: The Resurrection Project Link: Jack Crane - Senior Vice President - Director of Lending - Community Investment Corporation Link: Caste (Oprah's Book Club): The Origins of Our Discontents Link: AIA | Jack Cassin Link: Property Management Training – Community Investment Corporation ----------------- Guest Questions Lending Tip of the Month brought to you by Renovo Financial Landlord Tip of the Week 4:00 Renovo Value Add 5:45 How to get started as a new flipper? 5:50 What is CIC's mission? 10:15 In what way is CIC different from typical lenders? 13:30 Where do the CIC's funds come from? 16:35 What does the typical deal someone brings to CIC look like? 18:20 Are there lending requirements for deals CIC finances? 19:50 Once rehab is complete, do investors need to refinance out of the loan? 21:30 What's the minimum size of property the CIC will fund and what do you focus on? 22:00 What are some everyday type of activities that might qualify for energy grants? 27:00 What are some other reasons investors would work with CIC over other lending institutions? 28:50 Is there any comparison to the 80s uptown and rogers park in today's market? 32:00 What is the resurrection project? 35:13 Wrap Up Questions What is CIC's competitive advantage? 38:20 What is one piece of advice you'd give a new investor? 38:45 What do you do for fun? 39:10 What is a good self development activity you'd recommend to our listeners? 40:00 Who is one person in Chicago you'd recommend as a quality resource? 40:50 How can we learn more about you? 41:40 Chicago Fact 43:15 Thank you so much for listening. As always, we're here to help YOU. If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

How many ways are there to finance buying a property? Way more than I'm aware of which is why our guest Chris Puleo is here. With his robust 20+ year career, Chris has seen it all and explains a plethora of different popular products. With so much interest in househacking, of course we talk about the FHA product and calculating the self sufficiency tests. Not to mention some of the things investors AND brokers need to be aware of when putting offers on properties with an FHA loan product. Chris also compares the differences between buying in your personal name and buying in an LLC. There's a lot to unpack so let's get to it and if you like what you hear, or you learned something, please subscribe to our channel and give us a 5 star review. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: GC Realty & Development Guest: Chris Puleo of The Puleo Group Link: GC Realty & Development, LLC.: Chicago Property Management, Chicago Homes for Rent Link: Chris Puleo - The Puleo Group, Powered By Preferred Rate. NMLS 204168 | Call Chris | Email Chris ----------------- Guest Questions Landlord tip of the week 2:46 What are some differences between owner occupied and investment loans? 6:10 How have reserves changed before COVID vs now? 7:45 Can you talk about some of the contingencies regarding FHA loan for owner occupied properties? 9:20 Why is a 3 flat more difficult to underwrite than a 2 and 4 flat? 15:50 What are some risks FHA users need to consider when buying a property? 20:25 When would it make sense to buy down points on an FHA loan? 21:50 What are some differences between buying a property in a personal name vs an LLC? 24:20 Can you explain paydowns on wrap around loans and why a sale of one property would go to the debt of many properties? 26:50 What are some things you'd want to see from a new investor you've never done business with before? 30:00 What are some things that someone looking to househack should know when going to speak with you? 32:15 How do you think the lack of inventory has played into our current financing environment? 36:10 Wrap Up Questions What's your competitive advantage? 37:52 What is one piece of advice you'd give to a new investor? 39:00 What do you do for fun? 39:25 What is one good self development activity you would recommend to our listeners? 40:22 Who is one person you'd recommend from your local network? 41:10 How can we learn more about you? 42:50 That's our show! Thanks for tuning in once again! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.