About the Course
Introduction
This CLE/CPE course will provide attendees with an in-depth analysis of essential tax planning techniques for short-term rental properties. The panel will discuss the tax benefits of owning rental property, material participation rules, passive activity rules, criteria to ensure compliance with strict tax rules to maximize rental losses, aggregating rental properties, issues stemming from personal use of rental property, and other key tax planning considerations for short-term rentals.
Description
Short-term rentals offer unique opportunities to generate income and offset other earnings—but only when specific IRS requirements are met. This session will help attendees understand how to structure rental activities, navigate complex tax rules, and apply strategies involving entity selection, depreciation, and deductions to maximize tax efficiency and profitability. Counsel and tax professionals must understand complex tax rules for rental activities and certain exceptions to maximize tax savings.
The tax treatment of short-term rentals can vary depending on income classification, entity structure, depreciation, deductions, and other critical items. By navigating IRS rules and leveraging strategies, taxpayers could offset non-passive income while significantly increasing the profitability of their short-term rental properties.
Listen as our panel discusses the tax benefits of owning rental property, material participation and passive activity rules, maximizing rental losses, and other key tax planning considerations for short-term rentals.
Presented By
Mr. Kaufman joined Trout CPA in August 2020. He graduated Summa Cum Laude from Lebanon Valley College's 3+1 Accelerated Bachelor of Science in Accounting and MBA Program. Mr. Kaufman currently serves on the firm's Construction & Real Estate and Consumer Services industry groups. As a Manager, he assists with assurance services, including financial statement preparation, and provides tax planning and preparation support for individuals and corporations. Additionally, Mr. Kaufman specializes in helping real estate investors navigate the complexities of their financial and tax obligations.
Mr. Weaver joined Trout CPA in 2011 and brings over 20 years of accounting experience. A magna cum laude graduate of Millersville University, he is a Tax Partner and leads the firm’s Real Estate practice. Mr. Weaver specializes in advising commercial real estate investors, developers, and syndicates on entity structuring, tax-efficient strategies, and long-term wealth planning. He is widely recognized as a thought leader in real estate taxation, with expertise in commercial real estate, including multifamily, short-term rentals, and bonus depreciation. Mr. Weaver regularly authors through leadership articles and is a frequent podcast guest, sharing practical insights on tax strategies, entity formation, and maximizing investment returns.
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This 90-minute webinar is eligible in most states for 1.5 CLE credits.
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Date + Time
- event
Monday, May 18, 2026
- schedule
1:00 p.m. ET./10:00 a.m. PT
I. Applicable federal tax rules
II. Tax classification and structuring options
III. Depreciation, deductions, and other methods to minimize taxes
IV. State tax considerations
V. Best practices and planning considerations
The panel will discuss these and other key issues:
- Applicable federal tax rules and regulations impacting short-term rentals
- Potential entity structures and tax benefits
- Navigating ordinary versus passive income and traps to avoid
- Depreciation, deductions, and other methods to limit tax liability
- Practical strategies to maximize deductions and minimize tax liability
