The STR Tax & Compliance Map (US)

Understanding taxes starts with knowing what applies to you, and what doesn’t. In this session, we’ll look at the broader tax and compliance landscape for US-based short-term rental hosts, with a focus on how investors and experienced operators approach compliance decisions.

This event features Amanda Han and Matt MacFarland, both Managing Directors at Keystone CPA, and is hosted by Brandon Huetteman, Hospitable’s Accountant in Residence. Together, they’ll share how tax professionals think about STR planning, structure, and common red flags, all before things get complicated.

We’ll cover:

• How STR activity is generally treated from a tax perspective
• The STR “loophole”, how it’s commonly misunderstood, and the red flags hosts should be aware of
• Business structure considerations, including the role of LLCs
• How experienced investors approach tax planning and compliance

The session will begin with a guided discussion, followed by ample time for moderated Q&A.

About:

Amanda Han and Matt MacFarland are founders of Keystone CPA, where they advise real estate investors on tax strategy, structuring, and long-term planning. As both CPAs and investors, they focus on helping hosts and investors keep more of what they earn through thoughtful entity setup and tax planning. They are co-authors of the bestselling book "Tax Strategies for the Savvy Real Estate Investor", and frequent speakers and contributors across the real estate investing community.

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This session is part of Hospitable Unlocked: US Taxes & Compliance, a three-part series designed to help US-based short-term rental hosts develop a clearer, more confident understanding of taxes and compliance.

1. The STR Tax & Compliance Map (US) (February 10)
2. STR Taxes 101 (US): Income, Expenses, and Depreciation (February 24)
3. Staying Compliant All Year with Hospitable (March 10)