Tax Smart Real Estate Investors Podcast

Episode 349: How to Scale, Profit, and Survive in Today’s STR Market with Thanks for Visiting

Date: October 14, 2025
Host: Thomas (CPA/Tax Expert)
Guests: Annette Grant & Sarah Car, Co-founders of Thanks for Visiting

Episode Overview

This episode dives deep into how real estate investors can build, operate, and thrive in the today’s short-term rental (STR) market. Guests Annette Grant and Sarah Car, founders of the coaching platform Thanks for Visiting, share their journeys and impart critical wisdom on operational management, pricing, profitability, data-driven decisions, and navigating both tax strategies and business realities for STR operators.

Key Discussion Points & Insights

1. Getting Started in Short-Term Rentals

• Annette and Sarah’s Backgrounds
  • Annette and Sarah met as strangers at a city council meeting fighting for their right to do STRs—a testament to the importance of advocacy for STR operators.
    • Annette: "Showing up matters in this industry." (02:52)
  • Annette was a seasoned business builder seeking a scalable business and loved the security of real estate backed by a physical asset.
  • Sarah pivoted from a Broadway/HGTV background. She fell into STRs after realizing the financial potential—a move that propelled her from “blind confidence” into enthusiastic investment:
    • Sarah: “Unlike a roommate who just pays their portion of the mortgage, we got our mortgage covered and then some... as an actor...this was like the perfect fit for me, and I was all in.” (05:20–06:40)
  • Both now operate Thanks for Visiting, teaching hosts to run STRs as true businesses.

2. Biggest Keys to STR Profitability

• Top Priority: Dynamic Pricing and Calendar Management
  • Sarah: "Pricing and calendar management—none of you know how to do it and it is eating into your profits." (08:10)
  • Most hosts invest significantly in purchase and furnishing but neglect regular operational and financial oversight.
  • Annette: "They are business owners... once [hosts] make that connection, it changes what they focus on." (09:40)
• Mindset Shift: Treat it Like a Business
  • It’s essential to move beyond the “side hustle” mentality. Proactive, ongoing management is non-negotiable for success.

3. Actionable Advice for Busy STR Owners

• Daily, Weekly, Monthly Revenue Management

  • Annette: “Revenue management isn't about spreadsheets, it's about habits.” (12:44)
  • Like airlines and Uber, STR pricing should respond dynamically to demand, seasonality, and special events.
  • Owners must track—and account for—the value and cost of their own/family stays, especially during peak periods.

• Don’t Expect Month-One Profits

  • Chasing immediate profitability is unrealistic; STR is a seasonal business, and hosts must plan for fluctuations.
  • Annette: “Short term rentals cannot be a short term gain game… You have to be ready to play the long game.” (27:54, 28:47)

4. Bookkeeping and Tax Considerations

• Bookkeeping is Non-Negotiable and ‘Sexy’

  • Many STR hosts neglect or delay setting up professional bookkeeping, limiting their ability to make data-driven operational or tax decisions.
  • Annette: “The P&L is sexy when there is a big number at the bottom… we're doing this for the numbers.” (17:27)
  • Stay actively involved with your bookkeeper—don’t abdicate oversight.
  • Sarah: “Once you hire [a bookkeeper]... you have to stay on top of them... so you can then make decisions to pull different levers.” (18:14)

• Audit Risk and the Burden of Proof

  • Annette: “When you get audited...this is not like court where you're innocent until proven guilty. You are in the wrong until you can prove [you're] right.” (19:43)
  • Thomas: “You need to have impeccable records. ...if you get to the audit and you can't back this up...your credibility starts to diminish very quickly.” (20:41)
  • Evidence: Always keep time-logs for real estate professional status (REPS) or the STR loophole, and have organized financial records.

5. Key Performance Indicators (KPIs) that Matter

• Core KPIs Sarah and Annette Track:

  • Average Daily Rate (ADR)
  • Occupancy
  • RevPAN (Revenue per Available Night)
  • Booking Window
  • Average Length of Stay
  • Channel/source of booking (e.g., direct, OTA)

• Vanity Metrics Trap:

  • High occupancy can indicate underpricing.
    • Annette: “Volumes vanity, profit is sanity. That 100% occupancy to us is you are underpriced.” (25:15)
  • Profitability is the real metric that matters.

• Zoom Out: Consider Holistic Return

  • Wealth-building with STRs isn't just about cash flow, but also equity growth, tax advantages, and personal benefit.
    • Annette: “Please go, what is your home valued at right now vs. when you purchased it?” (26:37)
  • Know your "why"—whether appreciation, cash flow, or lifestyle.

Memorable Quotes & Moments

• On STR Not Being Passive:
  • Annette: “That’s a dose of realness we’re going to give today. ...They want passive income, and it’s not passive.” (15:36)
• On Unrealistic Expectations:
  • Annette: “They want the cash on cash return, they want the tax loophole, and they want to spend time in the property. And it doesn’t work like that.” (15:36)
• On Bookkeeping:
  • Sarah: “We have so many hosts...and they don’t have bookkeeping. ...I don’t know how you do that. I don’t think you can.” (16:04)
• On Education and Community:
  • Sarah: “If it were me, if I were to buy a short term rental, I would first want to know what I’m getting myself into, what to expect...I’d want to go in prepared.” (34:18)

Important Segments & Timestamps

• Guest Introductions & Origins in STR: 02:34–07:39
• Keys to Profitability: Pricing & Mindset: 08:08–10:47
• Realities of Passive vs. Active STR Investing: 15:36–16:46
• Bookkeeping, Audits, and REPS/STR Loophole Discussion: 16:46–22:29
• KPIs & Vanity Metrics: 23:23–25:56
• Zooming Out: Equity & Your STR “Why”: 26:37–28:47
• The Role of Education and When to Seek Help: 31:05–34:53

Summary Table: Top Takeaways

| Topic | Key Points | Notable Quote (Timestamp) | |-----------------------|----------------------------------------------------|----------------------------------| | Pricing | Use dynamic tools & habits. Don't underprice. | "Pricing and calendar management—none of you know how to do it..." (08:10) | | Mindset | Treat STR like a business, not a hobby/side gig. | "You are a business owner." (09:40) | | Bookkeeping | Must have clean books to make smart decisions; especially for audit defense. | "The P&L is sexy when there is a number at the bottom." (17:27) | | Data & KPIs | Focus on profit, not just occupancy; track several KPIs. | "Volumes vanity, profit is sanity..." (25:15) | | Tax Strategy | Keep records for REPS/STR loophole; burden of proof is on taxpayer. | "You are in the wrong until you can prove them right." (19:43) | | Long-Term Perspective | STRs are not get-rich-quick; play the long game. | "Short term rentals cannot be a short term gain game." (28:47) | | Holistic View | Consider equity, lifestyle, and appreciation, not just cash flow. | "Please go, what is your home valued at right now..." (26:37) |

Thanks for Visiting: Resources & Education

• Where to Find Annette & Sarah:
  • Thanks for Visiting Podcast
  • YouTube: Thanks for Visiting
  • Bootcamp Waitlist & Resources
• Who Should Join:
  • Anyone from “just considering” STR investing to experienced hosts can benefit from their free and paid educational content

Final Thoughts

This episode provides a realistic, actionable framework for making short-term rentals both successful and sustainable. The hosts and experts urge investors to shift from a “tax first” or “passive income” mindset to a comprehensive, business-owner approach—including ongoing pricing review, diligent financial management, and tracking the right performance metrics. Above all:

“Short term rentals cannot be a short term gain game. ...You have to be ready to play the long game.”
—Annette Grant (28:47)