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Straight Up Chicago Investor Podcast Episode 198 Part 2: 2023 Tax Strategies for Chicagoland Real Estate Investors with Michael Procaccio

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 of, as well as common mistakes and deductions that are frequently missed by landlords.

One key takeaway from this episode is the importance of staying updated on changes to the tax code, such as those relating to third payment softwares. Additionally, Michael emphasizes the need to understand the different types of tax statuses that can be held in order to make informed decisions.

Towards the end of the episode, Michael answers rapid-fire tax questions from the hosts, provides his competitive advantage, and gives advice for new investors. He also shares a book recommendation and encourages listeners to connect with him to learn more.

In summary, this podcast episode provides valuable insights into tax planning for real estate investors, including updates to the tax code, commonly missed deductions, and the importance of understanding different tax statuses.

Questions We Answer In this Show:

Q. What changes are there for real estate investors filing income taxes in 2023?

Q. Is Zelle, cash app, Venmo sending 1099s in 2023?

Q. Standard tax deductions rise with inflation in 2023?

Q. What should small Chicago landlords remember to write off as deductions?

Q. What are the 3 types of investors when it comes to taxable income?

Q. When do 1099 Forms have to be out to your contractors?

Show Notes:

  • 02:43 Housing Provider Tip: Utilize Chicago’s Prohibited Buildings List for due diligence on short term rentals!

  • 04:32 Intro to our guest, Michael Procaccio!

  • 06:22 What attracted Michael to investing in franchises?

  •  08:37 What advice would Michael give to someone new to franchise investing?

  • 10:17 Why did Michael get into accounting?

  • 12:12 What is new this year from an income tax perspective?

  • 13:56 Michael explains tax changes relating to third payment softwares!

  • 16:53 What are some commonly forgotten deductions by smaller scale landlords?

  • 19:12 Michael explains the different types of tax statuses!

  • 32:14 Tom asks Mike a series of tax related questions!

  • 37:29 What are some other frequently missed tax items?

  • 42:23 Are there new tax incentives for 2023?

  • 45:27 What is Michael's competitive advantage? 

  • 46:03 One piece of advice for new investors.

  • 47:04 What do you do for fun?

  • 48:10 Good book, podcast, or self development activity that you would recommend? 

  • 49:05 Local Network Recommendation?

  • 49:42 How can the listeners learn more about you and provide value to you?

  • Guest Name: Michael Procaccio

  • Guest Company: Pro Financial Services Group, Inc.

  • Guest Link:

  • Other Links for show notes:

  • Chicago's Prohibited Buildings List

  • Susan Camiliere (Real Estate Agent Recommendation)

  • Dave Schlueter (Attorney Recommendation)

  • Rick Tayfel (Lender Recommendation)

  • The Wealthy Gardner (Book Recommendation)

  • Michael’s Contact Info: / 630.924.2400

Chicago Investor Resources Shared

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