Maximizing Tax Benefits in Real Estate Syndication: Insights from Chip Simmonds, CPA

Unveiling Key Strategies for Investors

In a recent edition of TNL Talks hosted by Trowbridge Nieh LLP, Gene Trowbridge, Esq. CCIM sat down with Chip Simmonds, CPA, to delve into critical insights regarding syndication, crowdfunding, and navigating the intricate world of real estate investments. Chip, based in the San Antonio area, brings a wealth of experience and expertise to the table, shedding light on key strategies to maximize tax benefits and compliance in real estate ventures.

Understanding the New IRS Regulations

The discussion commenced with a deep dive into the latest regulations, particularly the requirement for LLCs and other reporting entities to register with the Financial Crimes Enforcement Unit (FinCEN) of the US Treasury Department under the recently enacted Corporate Transparency Act. Chip elucidated on the significance of this registration, its impact on business owners, and the meticulous process involved in providing beneficial ownership information.

It’s a bit of government overreach.

-Chip Simmonds, regarding the Corporate Transparency Act

“It’s a bit of government overreach,” remarked Chip, emphasizing the intricate details required for compliance and the associated fines for non-registration.

For more insights on this topic, watch the full discussion here.

Navigating Passive Loss Rules and Tax Planning

Chip and Gene further explored the nuances of passive loss rules, outlining how investors can navigate these regulations to optimize tax benefits. They discussed the interplay between passive income and passive losses, highlighting the importance of Form 8582 in tracking and utilizing suspended losses effectively.

“It’s a timing game,” noted Gene, emphasizing the significance of strategic tax planning and leveraging suspended losses against future gains.

Unlocking New Tax Saving Opportunities

Chip unveiled two new tax-saving opportunities for taxpayers in 2024, including the simplified per mileage rate for business use of personal vehicles and the revamped per diem travel rate. These initiatives provide simplified mechanisms for taxpayers to claim deductions, reducing the complexity of record-keeping and enhancing tax efficiency.

Consultation with TNL Attorneys

For personalized guidance on syndication, crowdfunding, and navigating the intricacies of real estate investments, consider scheduling a consultation with a Trowbridge Nieh LLP attorney. Our team of experts is dedicated to helping clients ensure compliance and choosing the correct registration exemption for their real estate and private investment ventures.


Navigating the complexities of real estate syndication, crowdfunding, and private investments requires a comprehensive understanding of IRS regulations and strategic tax planning. Through insightful discussions with experts like Chip Simmonds, CPA and Gene Trowbridge, Esq. CCIM, investors can gain valuable insights and unlock opportunities to optimize tax benefits while ensuring compliance. Stay informed, plan strategically, and leverage expert guidance to maximize returns on real estate investments.

Relevant Insights

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