Jonathan On Money10 Sep 2025

Episode 125: IN FOCUS: Tax Issues with Distressed Real Estate with Matthew E. Rappaport (Falcon Rappaport & Berkman LLP)

Join Jonathan I. Shenkman, President & CIO of ParkBridge Wealth Management, as he goes “IN FOCUS” to explore more advanced wealth planning topics.

This week, we will go IN FOCUS where we will cover more advanced wealth planning topics.

Today, we are joined by Matthew E. Rappaport, Esq., LL.M. of Falcon Rappaport & Berkman LLP based in Long Island, New York. Matthew will be discussing “Tax Issues with Distressed Real Estate.”

By way of background, this timely discussion will provide a comprehensive overview of distressed real estate transactions, focusing on their tax implications and strategic considerations. Key topics that will be covered include debt restructuring and the tax treatment of foreclosures, sales, and deed-in-lieu transactions. Matt will also explore how bankruptcy, solvency/insolvency, and receiverships affect the tax treatment of various distressed real estate transactions. Additionally, Matthew will highlight the application of §1031 exchanges in distressed real estate, assessing their feasibility based on various factors.

***UPCOMING LIVE WEBINAR: on Thursday, September 18th @ 8:30am (New York time) featuring Bruce D. Steiner, Esq., LL.M., Of Counsel at Kleinberg, Kaplan, Wolff & Cohen, P.C. based in New York City. Bruce will be speaking on “Snowbird Domicile and Choice Of Law.” Register here: https://us02web.zoom.us/webinar/register/WN_rQszYJ7sQeqHiaP6EsLU2A***

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