178. “Truth About Investing in Short Term Rentals” with Anne Gannon Artwork

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178. “Truth About Investing in Short Term Rentals” with Anne Gannon

June 25, 2025 • Dawn Kennedy • Season 1 • Episode 178

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Dawn Kennedy talks with Anne Gannon, CPA, who is not your typical accountant. A former professional golfer, she began her career as a CPA with a big-five accounting firm in Boston, Massachusetts. There, she quickly realized that the only winner in the traditional “busy season” approach was the accounting firm. Dawn and Anne talk about how short-term rentals can generate revenue, the risks involved, and the importance of planning and understanding regulations. The episode provides valuable insights into the benefits and challenges of managing short-term rentals, including tax advantages and the importance of finding the right property and location.

Who is Anne Gannon, and whom does she serve? (0:55)

Short‑Term Rentals as Investments (1:29)

Risks and Rewards of Short‑Term Rentals (2:19)

Location Considerations for Short‑Term Rentals (7:18)

Legalities and Regulations (13:23)

Tax Benefits and the Accounting Perspective (17:31)

Consumer Behavior and Market Trends (21:47)

Conclusion and Contact Information (30:14)

Anne Gannon’s information:

Phone: (617) 943-0480

Website: https://www.accelerator-method.com/

LinkedIn: https://www.linkedin.com/in/anne-gannon-529107148/