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Straight Up Chicago Investor Podcast Episode 202: Challenging Househacks With Sewer Lines, Evictions...

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Our latest podcast episode features Ben Sussman, a real estate investor who has acquired 12 investment properties before the age of 30. While building a real estate portfolio at a young age may sound glamorous, Ben gave us a raw, unfiltered look at the challenges he has faced and the hard-won lessons he has learned along the way.Ben got into real estate investing because he was attracted to the cash flow and tax benefits. He started by ...

Straight Up Chicago Investor Podcast Episode 201: Should You Move Your Rental Property to an LLC?

When you own a rental property, you are taking on a certain amount of risk. If something goes wrong, such as a tenant getting injured on your property, you could be held liable. This could mean losing your property, your savings, and even your home.One way to protect yourself from this risk is to move your rental property to an LLC. An LLC is a type of business entity that provides limited liability to its owners. This means that if som...

Straight Up Chicago Investor Podcast Episode 200: Which Chicago Neighborhoods are Hot and Which are ...

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Welcome to Episode 200 of our Chicago Real Estate Podcast! In this milestone episode, we've got an incredible panel discussion with Matt Feo, Jake Fugman, and Blake McCreight. Our experts will take you through a journey of Chicago's hottest real estate markets and give you insider knowledge on which neighborhoods are set to double in value.We know that the real estate market can be unpredictable, but our panel will help you stay...

Straight Up Chicago Investor Podcast Episode 199: Lincoln Yards: A Sterling Bay Project Transforming...

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If you're a Chicagoan, then you've probably heard about the massive Lincoln Yards development project, which is set to transform the North Branch of the Chicago River. The 53-acre mixed-use community development by Sterling Bay has been the talk of the town for a while now.In this podcast episode, Matt Menna, the Managing Principal of Sterling Bay, joins the discussion to shed more light on the project. Matt starts by ...

Straight Up Chicago Investor Podcast Episode 198 Part 2: 2023 Tax Strategies for Chicagoland Real Es...

Tax planning is a crucial aspect of real estate investing that can significantly impact your bottom line. To provide insight into optimal tax planning, Michael Procaccio, a tax advisor and Chicagoland investor, joins this podcast episode.Michael begins by discussing his accounting career and how he became involved in investing in franchises. He then goes on to explain the latest changes to the tax code that investors can take advantage ...

Straight Up Chicago Investor Podcast Episode 198: 2023 Tax Strategies for Chicagoland Real Estate In...

Tax season can often be a stressful time for many individuals, but with the right planning and advice, it can also be a time to increase your bottom line. This is where Michael Procaccio, a tax advisor and Chicagoland investor, comes in to provide his insightful expertise on optimal tax planning.In this full episode video, Michael delves deep into the world of tax planning and highlights the different strategies individuals can use to m...

Straight Up Chicago Investor Podcast Episode 197: Four Mistakes To Avoid When Underwriting Multifami...

Multifamily property underwriting can be a complex process with many factors to consider. As an underwriter, it's important to be aware of common mistakes that can lead to inaccurate valuations or inefficient use of time and resources. Here are four mistakes to avoid when underwriting multifamily properties:1. Relying too heavily on historical data2. Overlooking physical and operational risks3. Ignoring environmental factors4. Under...

Straight Up Chicago Investor Podcast Episode 196: Going A-to-Z on a Sight Unseen Purchase and Gut Re...

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Are you considering buying a multifamily building without physically seeing it? John Warren’s experience with his purchase and gut renovation in Cicero can give you an insight into what to expect.Underwriting and estimating rehab costs are the very first steps in making an offer. John Warren shares that it’s important to factor in the potential costs and risks involved in such a purchase. Once the purchase is made, a Cicero ...

Straight Up Chicago Investor Podcast Episode 196: Going A-to-Z on a Sight Unseen Purchase and Gut Re...

Are you considering buying a multifamily building without physically seeing it? John Warren’s experience with his purchase and gut renovation in Cicero can give you an insight into what to expect.Underwriting and estimating rehab costs are the very first steps in making an offer. John Warren shares that it’s important to factor in the potential costs and risks involved in such a purchase. Once the purchase is made, a Cicero ...

Straight Up Chicago Investor Podcast Episode 195: Building $300k in Networth Through House Hacking (...

Victoria Barkate joins us to discuss how she has quickly scaled her rental property portfolio as a W2 employee!Victoria starts by explaining her decision to move to Chicago specifically to invest in real estate. She talks about how she decided which neighborhoods to invest in and how she has utilized partnerships to scale She dives into the ins-and-outs of her first couple house hacks including things that went well and challenges she f...
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