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.

>> Register here.

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)